以開發各類5,6-芳香環并香豆素與7,8-芳香環并香豆素的合成方法，並將其應用於天然物Angelicin, Seselin, Xanthxyletin and Psoralen的製備。

Various synthetic methods of benzocoumarins are described in this study.
In chapter 2, we have developed a new and useful method of preparing 5,6-benzocoumarins (2–2g) with different substituents on a variety of positions. Their molecular skeletons were formed from the oxidation of 2H-pyrans by DDQ reagent. These 2H-pyrans were prepared by tandem reaction of cis-hydrogenation of enynals and electrocyclization. Various α-tetralones were used as starting materials. Heteroarene-fused coumarins (2h–2k) were also prepared respectively.
In chapter 3, a modified synthetic route – α-tetralone keto ester was catalyzed by DBU– for Michael addation is described. The results
not only represent sizable yield of 7,8-benzocoumarins (3–3g, 22b, 22c, 26) under convenient conditions, but also provide an efficient route for the synthesis of some natural products, such as Angelicin (28), Seselin (33), and Pyrone (39, 39d).
In chapter 4, a new benzocoumarin building block method from β-tetralone has been discovered, under the condition of propiolic acid and HOTf, to give Claisen rearrangement products. The 5,6-benzocoumarin carbon skeleton from substituted β-tetralone was built up in 2 steps.
In final chapter, previous reaction condition was carried out naphthols and meta-substituted phenols. Aromatic coumarins (63–79) and some natural products (83, 87) were prepared respectively.

目錄
摘要 ------------------------------------------------------------------- I
目錄 ------------------------------------------------------------------------- V
圖表目錄 ------------------------------------------------------------- IX
縮寫對照表 ------------------------------------------------------------ X V I I
第一章 緒論 -------------------------------------------------------------- P. 1
1.1 背景介紹 -------------------------------------------------------- P. 1
1.2 研究緣起 -------------------------------------------------------- P. 2
1.3 文獻報導 ------------------------------------------------ P. 5
1.3.1 傳統方法合成香豆素 ----------------------------------------- P. 5
1.3.2 利用金屬催化合成香豆素 ------------------------------ P. 20
1.3.3 香豆素類化合物的研究與發展 ---------------------------- P. 36
1.3.4 以香豆素為螢光材料的發展與應用 ----------------------- P. 50
第二章 從1-四氫酮開始—獲得5,6-苯并香豆素的研究與方法 ------ P. 56
2.1 研究背景 ------------------------------------------------------------- P. 56
2.2策略I之逆合成分析:【由1-tetralone合成5,6-benzocoumarin】 --- P. 59
2.3 結果與討論 ------------------------------------------------ P.65
2.3.1【5,6-苯并香豆素的合成】-------------------------------------- P.65
2.3.2【5,6-雜環并香豆素的合成】------------------------------------ P.68
2.3.3【5,6-多環并香豆素的合成】----------------------------------- P. 71
2.3.4【進行其他實驗的研究】----------------------------------- P. 78
2.4策略II之逆合成分析:【由2-tetralone合成7,8-benzocoumarin】---- P.80
2.5 結果與討論 ----------------------------------------------- P.82
2.5.1【7,8-苯并香豆素的合成研究】------------------- P.82
2.6 結論 --------------------------------------------------------------- P. 84
第三章 從1-四氫酮開始—獲得7,8-苯并香豆素的研究與方法 ----- P. 86
3.1 研究背景 -------------------------------------- P. 86
3.2策略III之逆合成分析:
【由1-tetralone合成7,8-benzocoumarin (一)】------------------ P. 87
3.3 結果與討論【7,8-苯并香豆素的合成 (一)】 -------------------- P. 88
3.4策略III-2之逆合成分析:
【由1-tetralone合成7,8-benzocoumarin (二)】 ----------------- P. 95
3.5 結果與討論【7,8-苯并香豆素的合成 (二)】------------------ P. 96
3.6策略III-3之逆合成分析:
【由1-tetralone合成7,8-benzocoumarin (三)】------------------ P. 99
3.7 結果與討論【7,8-苯并香豆素的合成 (三)】------------------- P. 100
3.7.1【合成7,8-苯并香豆素的例子】 ---------------------- P. 107
3.7.2【合成7,8-雜環并香豆素的例子】----------------------- P. 108
3.7.3【應用至合成吡喃酮(Pyrone)的例子】---------------------- P. 114
3.7.4【進行其他實驗的研究】------------------------------- P. 119
3.8 結論 ------------------------------------------------------------ P. 120
第四章 從β-四氫酮開始—獲得5,6-苯并香豆素的研究與方法 --- P. 121
4.1 研究背景 ------------------------------------------------------------ P. 121
4.2策略IV之逆合成分析:
【由β-tetralone合成5,6-benzocoumarin (一)】--------- P. 122
4.3 結果與討論【5,6-苯并香豆素的合成 (一)】------------------- P. 123
4.4策略IV-2之逆合成分析:
【由β-tetralone合成5,6-benzocoumarin (二)】----------- P. 126
4.5 結果與討論【5,6-苯并香豆素的合成 (二)】---------------- P. 127
4.6策略IV-3之逆合成分析:
【由β-tetralone合成5,6-benzocoumarin (三)】------------------ P. 133
4.7 結果與討論【5,6-苯并香豆素的合成 (三)】--------------- P. 134
4.8策略IV-4之逆合成分析:
【由2-tetralone合成5,6-benzocoumarin (四)】------------------------ P. 135
4.9 結果與討論【5,6-苯并香豆素的合成 (四)】--------------- P. 136
4.10 結論 ------------------------------------------------------------ P. 139
第五章 從萘酚開始—一鍋化獲得多苯并香豆素的研究與方法 --- P.140
5.1 研究背景 -------------------------------------- P. 140
5.2 結果與討論【多芳香環并香豆素的合成】 ------------- P. 142
5.3 結果與討論【雜環并香豆素的合成】-------------- P. 159
5.4 結論 -------------------------------------------------------------P. 166
實驗 ---------------------------------------------- P. 167
(Uv-Vis)吸收與螢光放射量測 -------------------- P. 213
光譜數據 -------------------------------- P. 230
參考文獻 ----------------------------------------- P. 363
NMR圖譜 -------------------------------- P. 374

參考文獻
1. (a) Murray, R. D. H.; Mendez, J.; Brown, S. A. The Natural Coumarins: Occurrence, Chemistry, and Biochemistry; Wiley: New York, 1982. (b) Naser-Hijazi, B.; Stolze, B.; Zanker, K. S. Second Proceedings of the International Society of Coumarin Investigators; Springer: Berlin, 1994. (c) Hepworth, J. D. In Comprehensive Heterocyclic Chemistry; Katritzky, A.; Rees, C. W.; Boulton, A. J.; Mckillop, A., Eds.; Pergamon Press: Oxford, 1984; Vol. 3, Chapter 2.24, 799–810.
2. (a) 鄭佳怡，新的芳香環并香豆素合成方法開發與研究，民國九十六年(2007)國立中正大學化學暨生物化學學系碩士論文。(b) Hon, Y. S.; Hsu, Y. C.; Cheng, C. Y. J. Chin. Chem. Soc. 2006, 53, 1447–1462. (c) 徐仁生，葉陽，趙維民 天然產物化學(第二版) 2004年北京：科學出版社，589–610。
3. for Pechmann condensation:
(a) Pechmann, H. V.; Duisberg, C. Chem. Ber. 1883, 16, 2119. (b) Pechmann, V. H.; Duisberg, C. Chem. Ber. 1884, 17, 929 (c) De, S. K.; Gibbs, R. A. Synthesis 2005, 1231–1233. (d) Potdar, M. K.; Mohile, S. S.; Salunkhe, M. M. Tetrahedron Lett. 2001, 42, 9285–9287. (e) Rajitha, B.; Kumar, V. N.; Someshwar, P.; Madhav, J. V.; Reddy, P. N.; Reddy, Y. T. ARKIVOC 2006, 23–27. (f) George, A. Synthesis 2008, 2871–2873. (g) Symeonidis, T.; Chamilos, M.; Hadjipavlou-Litina, D. J.; Kallitsakis, M.; Litinas, K. E. Bioorg. Med. Chem. Lett. 2009, 19, 1139–1142. (h) Bose, D. S; Rudradas, A. P.; Babu, M. H. Tetrahedron Lett. 2002, 43, 9195–9198. (i) Sun, P.; Hu, Z. Synth. Commun. 2005, 35, 1875–1880. (j) Singhal, S; Jain, S. L.; Sain, B. Heterocycles 2008, 75, 1205–1211. (k) Valizadeh, H.; Shockravi, A. Tetrahedron Lett. 2005, 46, 3501–3504. (l) Bahekar, S. S.; Shinde, D. B. Tetrahedron Lett. 2004, 45, 7999–8002. (m) Ghosh, K.; Adhikari, S. Tetrahedron Lett. 2006, 47, 8165–8169. (n) Aquila, B. M. Tetrahedron Lett. 1997, 38, 2795-2798. (o) Curini, M.; Epifano, F.; Maltese, F.; Marcotullio, M. C.; Tubaro, A.; Altinier, G.; Gonzales, S. P.; Rodriguez, J. C. Bioorg. Med. Chem. Lett. 2004, 14, 2241–2243. (p) Wang, Y.; Huang, S. X.; Xia, P.; Xia, Y.; Yang, Z. Y.; Kilgore, N.; Morris-Natschke, S. L.; Lee, K. H. Bioorg. Med. Chem. Lett. 2007, 17, 4316–4319. (q) Melliou, E.; Magiatis, P.; Mitaku, S.; Skaltsounis, A. L.; Chinou, E.; Chinou, I. J. Nat. Prod. 2005, 68, 78–82. (r) Chang, C. F.; Yang, L. Y.; Chang, S. W.; Fang, Y. T.; Lee, Y. J. Tetrahedron 2008, 64, 3661–3666. (s) Chavan, S. P.; Shivasankar, K.; Sivappa, R.; Kale, R. Tetrahedron Lett. 2002, 43, 8583–8586. (t) Romanelli, G. P.; Bennardi, D.; Ruiz, D. M.; Baronetti, G.; Thomas, H. J.; Autino, J. C. Tetrahedron Lett. 2004, 45, 8935–8939.
4. for Perkin reaction:
(a) Perkin, W. H. J. Chem. Soc. 1868, 21, 53. (b) Perkin, W. H. J. Chem. Soc. 1877, 31, 388–427. (c) Tan, T. F.; Han, J.; Pang, M. L.; Fu, Y. F.; Ma, H.; Ma, Y. X.; Meng, J. B. Tetrahedron 2006, 62, 4900–4906. (d) Valenti, P.; Rampa, A.; Budriesi, R.; Bisi, A.; Chiarini, A. Bioorg. Med. Chem. 1998, 6, 803–810. (e) Rao, C. B.; Subramanyam, G.; Venkateswarlu, V. J. Org. Chem. 1959, 24, 685–687.
5. for Knoevenagel condensation:
(a) Jones, G. Org. React. 1967, 15, 204–599. (b) Adams, R.; Bockstahler, T. E. J. Am. Chem. Soc. 1952, 74, 5346–5348. (c) Posakony, J.; Hirao, M.; Stevens, S.; Julian A. Simon, J. A.; Bedalov, A. J. Med. Chem. 1959, 47, 2635–2644. (d) Bogda, D. J. Chem. Research (S), 1998, 468–469. (e) Ranu, B. C.; Jana, R. Eur. J. Org. Chem. 2006, 3767–3770.
6. for Wittig reaction:
(a) Narasimhan, N. S.; Mali, R. S. Tetrahedron 1975, 31, 1005–1009. (b) Harayama, T. Chem. Pharm. Bull. 2000, 54, 543–564.(日文版) (c) Horaguchi, T.; Hosokawa, N.; Tanemura, K.; Suzuki, T. J. Heterocyclic. Chem. 2002, 39, 61–67.
7. other method:
(a) Sato, K.; Amakasu, T. J. Org. Chem. 1968, 33, 3767–3770. (b) Rao, H. S. P.; Sivakumar, S. J. Org. Chem. 2006, 71, 8715–8723. (c) Yavari, I.; Hekmat-Shoar, R.; Zonouzi, A. Tetrahedron Lett. 1998, 42, 2391–2392. (d) Harvey, R. G.; Cortez, C.; Ananthanatayan, T. P.; Schmolka, S. J. Org. Chem. 1988, 53, 3936–3943. (e) Taylor, R. T.; Cassell, R. A. Synthesis 1982, 672–673. (f) Panetta, J. A.; Rapoport, H. J. Org. Chem. 1982, 47, 946–950.
8. for Friedel-Crafts reaction:
(a) Liao, Y.; Hendrata, S.; Bae, S. Y.; Wang, B. Chem. Pharm. Bull. 2000, 48, 1138–1147. (b) Kalinin, A. K.; da Silva, A. J. M.; Lopes, C. C.; Lopes, R. S. C.; Snieckus, V. Tetrahedron Lett. 1998, 39, 4995–4998. (c) Lee, J. M.; Tseng, T. H.; Lee, Y. J. Synthesis 2001, 15, 2247–2254.
9. for Pd:
(a) Trost, B, M.; Toste, F, D. J. Am.Chem. Soc. 1996, 118, 6305–6306. (b) Trost, B, M.; Toste, F, D.; Greenman, K. J. Am.Chem. Soc. 2003, 125, 4518–4526. (c) Kadnikov, D. V.; Larock, R. C. Org. Lett. 2000, 2, 3643–3646. (d) Kadnikov, D. V.; Larock, R. C. J. Org. Chem. 2003, 68, 9423–9432. (e) Jia, C.; Lu, W.; Oyamada, J.; Kitamura, T.; Matsuda, K.; Irie, M.; Fujiwara. Y. J. Am.Chem. Soc. 2000, 122, 7252–7263. (f) Jia, C.; Piao, D.; Kitamura, T.; Fujiwara, Y. J. Org. Chem. 2000, 65, 7516–7522. (g) Hesse, S.; Kirsch, G. Tetrahedron Lett. 2002, 43, 1213–1215. (h) Palencia, H.; Garcia-Jimeneza, F.; Takacsb, J. M. Tetrahedron Lett. 2004, 45, 3849–3853. (i) Battistuzzi, G.; Cacchi, S.; Salve, I, D.; Fabrizi, G.; Parisi, L. M. Adv. Synth. Catal. 2005, 347, 308– 312. (j) Raad, I.; Terreux, R.; Richomme, P.; Matera, E. L.; Dumontet, C.; Raynauda, J.; Guileta, D. Bioorg. Med. Chem. 2006, 14, 6979–6987. (k) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992–1995.
10. for Ru:
(a) Chatterjee, A. K.; Toste, F. D.; Goldberg, S. D.; Grubbs, R. H. Pure Appl. Chem. 2003, 75, 421–425. (b) Van, T. N.; Debenedetti, S.; Kimpe, N. D. Tetrahedron Lett. 2003, 44, 4199–4201.
11. for Pt:
(a) Oyamada, J.; Kitamura, T. Tetrahedron Lett. 2005, 46, 3823–3827. (b) Oyamada, J.; Kitamura, T. Tetrahedron 2006, 62, 6918–6925. (c) Pastine, S. J.; Youn, S. W.; Sames, D. Org. Lett. 2003, 5, 1055–1058.
12. for Au:
(a) Shi, Z.; He, C. J. Org. Chem. 2004, 69, 3669–3671. (b) Huo, X.; Ren, X.; Xu, Y.; Li, X.; She, X.; Pan, X. Tetrahedron : Asymmetry 2008, 19, 343–347. (c) Wegner, H. A.; Ahles, S.; Neuburger, M. Chem. Eur. J. 2008, 14, 11310–11313. (d) Menon, R. S.; Findlay, A. D.; Bissember, A. C.; Banwell, M. G. J. Org. Chem. 2009, 74, 8901–8903.
13. for Rh: Yoneda, E.; Sugioka, T.; Hirao, K.; Zhang, S. W.; Takahashi, S. J. Chem. Soc., Perkin Trans.1 1998, 477–483
14. for Ni: Rayabarapu, D. K.; Shukla, P.; Cheng, C. H. Org. Lett. 2003, 5, 4903–4906.
15. for Yb: Fillion, E.; Dumas, A. M.; Kuropatwa, B. A.; Malhotra, N. R.; Sitler, T. C. J. Org. Chem. 2006, 71, 409–412.
16. for In: Kalyanam, N.; Nagarajan, A.; Majeed, M. Synth. Commun. 2006, 34, 1909–1914.
17. for Hf: Song, C. E.; Jung, D. U.; Choung, S. Y.; Roh. E. J.; Lee, S. G. Angew. Chem. Int. Ed. Engl. 2004, 43, 6183–6185.
18. for Cu: Yamamoto, Y.; Kirai, N. Org. Lett., 2008, 10, 5513–5516.
19. for Fe: Li, R.; Wang, S. R.; Lu, W. Org. Lett. 2007, 9, 2219–2222.
20. (a) Deshpande, P. P.; Tagliaferri, F.; Victory, S. F.; Yan, S.; Baker, D. C. J. Org. Chem. 1995, 60, 2964–2965. (b) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 9074–9075. (c) Tanaka, Y.; Kumamoto, T.; Ishikawa. T. Tetrahedron Lett. 2000, 41, 10229–10232.
21. (a) Shikishima, Y.; Takaishi, Y.; Honda, G.; Ito, M.; Takeda, Y.; Kodzhimatov, O. K.; Ashurmetov, O.; Lee, K. H. Chem. Pharm. Bull. 2001, 49, 877–880. (b) Hayakawa, K.; Yodo, M.; Ohsuki, S.; Kanematsu, K. J. Am. Chem. Soc. 1984, 106, 6735–6740. (c) Stanjek, V.; Miksch, M.; Lueer, P.; Matern, U.; Boland, W. Angew. Chem. Int. Ed. Engl. 1999, 38, 400–402. (d) Zou, Y.; Lobera, M.; Snider, B. B.
J. Org. Chem. 2005, 70, 1761–1770. (e) Chimichi, S.; Boccalini, M.; Cosimelli, B.; Viola, G.; Vedaldi, D.; Dall'Acqua, F. Tetrahedron 2002, 58, 4859–4863.
22. (a) Wulff, W. D.; McCallum, J. S.; Kunng, Fen-A. J. Am. Chem. Soc. 1988, 110, 7419–7434. (b) Sardari, S.; Mori, Y.; Horita, K.; Micetich, R. G.; Nishibe, S.; Daneshtalab, M Bioorg. Med. Chem. 1999, 7, 1933–1940. (c) Clarke, D. J.; Robinson, R. S. Tetrahedron 2002, 58, 2831–2837.
23. (a) Nicolaou, K. C.; Pfefferkorn, Jeffrey A.; Cao, G. Q. Angew. Chem. Int. Ed. Engl. 2000, 39, 734–739. (b) Bulman Page, P. C.; Appleby, L. F.; Day, D.; Chan, Y.; Buckley, B. R.; Allin, S. M.; McKenzie, M. J. Org. Lett. 2009, 11, 1991–1993. (c) Zhou, T.; Shi, Q.; Lee, K. H. Tetrahedron Lett. 2010, 51, 4382–4386.
24. (a) Kim, S.; Ko, H.; Son, S.; Shin, K. J.; Kim, D. J. Tetrahedron Lett. 2001, 42, 7641–7643. (b) Lee, J. H.; Bang, H. B.; Han, S. Y.; Jun. J. G. Tetrahedron Lett. 2007, 48, 2889–2892. (c) Baldoumi, V.; Gautam, D. R.; Litinas, K. E.; Nicolaides, D. N. Tetrahedron 2006, 62, 8016–8020. (d) Nicolaou, K. C.; Pfefferkorn, J. A.; Roecker, A. J.; Cao, G. Q.; Barluenga, S.; Mitchell, H. J. J. Am. Chem. Soc. 2000, 122, 9939–9953.
25. (a)盧凌；王仁宗；張榮錡；王金漢；莊昭文；陶占瑞 化學 2000，
58，367–385。(b) Pope, M.; Kallmann, P. J. Chem. Phys. 1963, 38 2042. (c) 陳丁洲，聚雙噻吩環戊烷衍生物的合成與性質探討，民國九十三年(2004)國立中央大學化學系碩士論文。
26. (a) Fujikawa, H. “Efficient Orange Organic Light-Emitting Diodes Doped with Coumarin Dyes”, R&D Review of Toyota CRDL, 2002, 37, 71. (b) Schimimitschek, E. J.; Trias, J. A.; Hammond, P. R.; Atkins, R. L. Opt. Commun. 1974, 11, 352. (c) Fletcher, A. N. ; Hollins, R. A.; Kubin, R. F.; Henry, R. A.; Atienza Moore, T. M.; Pietrak, M. E. Appl. Phys. B. 1983, 30, 195. (d) Fox, J. L.; Chen, C. H. US Patent 4736032, 1988; (e) Inoe, T.; Nakatani, K. Japan Patent 6009952, 1994 (f) Tto, J. Japan Patent 7166169, 1995. (g) OLED/有機電激發光材料與元件 黃孝文,陳金鑫,五南圖書, 2005年9月。(h) Ho, M. H.; Wu, Y. S.; Wen, S. W.; Lee, M. T.; Chen, T. M.; Chen, C. H.; Kwok, K. C.; So, S. K.; Z.; Gao, Z. Q. Applied Phy. Lett. 2006, 89, 252903.
27. (a) Feuster, E. K.; Glass, T. E. J. Am. Chem. Soc. 2003, 125, 16174–16175. (b) Chen, C. T.; Huang, W. P. J. Am. Chem. Soc. 2002, 124, 6246–6247. (c) Klein, G.; Reymond, J. L. Bioorg. Med. Chem. Lett. 1998, 8, 1113–1116. (d) Kulatilleke, C. P.; de Silva, S. A.; Eliav, Y. Polyhedron 2006, 25, 2593. (e) Schiedel, M. S.; Briehn, C. A.; Bäuerle, P. Angew. Chem. Int. Ed. 2001, 40, 4677–4680. (f) Wheelock, C. E. J. Am. Chem. Soc. 1958, 9, 1348–1352.
28. (a) Rahman, S. M.; Kobayashi, T. Molecules 2002, 7, 840–847. (b) Bull. Korean Chem. Soc. 2008, 29, 2513–2516. (c) Fatiadi, A. J. Synthesis 1987, 2, 85–127.
29. (a) Chen, C. P.; Swenton, J. S. J. Org. Chem. 1988, 53, 3936–3943. (b) Combs, D. W.; Cornelius, L. A. M. Synth. Commun. 1994, 24, 2777–2788. (c) Esteban, G.; Mpez-Sarrchez, M. A.; Martinez, M. E.; Plumet, E. Tetrahedron 1998, 54, 197–212. (d) Premasagar, V.; Palaniswamy, V. A.; Eisenbraun, E. J. J. Org. Chem. 1981, 46, 2974–2976. (e) Zambias, R. A.; Caldwell, C. G.; Kopka, I. E.;
Hammond, M. L. J. Org. Chem. 1988, 53, 4135–4137. (f) Huang, Y.; Hartmann, R. W. Synth. Commun. 1998, 28, 1197–1200. (g) Sissouma, D.; Collet, S. C.; Guingant, A. Y. Synlett 2004, 2612–2614. (h) Maertens, F.; Bogaert, A. V.; Compernolle, F.; Hoornaert, G. J. Eur. J. Org. Chem. 2004, 4648–4656. (i) Bobbitt, J. M.; Kulkarni, C. L.; Dutta, C. P.; Kofod, H.; Chiong, K. N. J. Org. Chem. 1978, 43, 3541–3544. (j) Cornelius, L. A. M.;Combs, D. W. Synth. Commun. 1994, 24, 2777–2788. (k) Makosza, M.; Kwast, E. Tetrahedron 1995, 51, 8339–8354. (l) Chen, C. P.; Swenton. J. S. J. Org. Chem. 1985, 50, 4569–4576. (m) Wilds, A. L. J. Am. Soc. Chem. 1942, 64, 1421–1427. (n) Ho, J. H.; Lin, J. H.; Ho, T. I. J. Chin. Chem. Soc. 2005 , 52, 805–810.
30. (a) Maynard, D. F.; Okamura, W. H. J. Org. Chem. 1995, 60, 1763. (b) Beaudry, C. M.; Malerich, J. P. Trauner, D. Chem. Rev. 2005, 105, 4757. (c) Worlikar, S. A.; Kesharwani, T.; Yao, T.; Larock, R. C. J. Org. Chem., 2007, 72, 1347. (d) Fan, M.; Yan, Z.; Liu, W.; Liang, Y. J. Org. Chem. 2005, 70, 8204. (e) Menz, H.; Kirsch, S. F. Org. Lett. 2006, 8, 4795. (f) Olah, G. A.; Keumi, T.; Lecoq, J. C.; Fung, A. P,; Olah, J. A. J. Org. Chem. 1991, 56, 6148. (g) Ameer, F.; Green, I. R.; Krohn, K.; Sitoza, M.; Synth. Commun. 2007, 37, 3041. (g) Essiz, M.; Guillaumet, G.; Brunet, J. J.; Caubere, P. J. Org.Chem. 1980, 45, 240.
31. (a) Cuiotto, A.; Manzini, P.; Chilin, A.; Pastorini, G.; Rodighiero, P. J. Heterocyclic. Chem. 1985, 22, 649–656. (b) Harayama, T.; Nishita, Y. Chem. Phram. Bull. 1996, 44, 1986–1988.
32. Hon, Y. S.; Tseng, T. W.; Cheng, C. Y. Chem. Commun. 2009, 5618–5620.
33. (a) Posner, G. H.; Sterling, J. J. J. Am. Chem. Soc. 1973, 95, 3076–3077. (b) Stork, G.; Rosen, P.; Goldman, N. L. J. Am. Chem. Soc. 1961, 83, 2965–2966. (c) Ackrell, J.; Muchowski, J. M.; Galeazzi, E.; Guzman, A. J. Org. Chem. 1986, 51, 3374–3376. (d) Henoch, F. E.; Hampton, K. G.; Hauser, C. R. J. Am. Chem. Soc. 1969, 91, 676–681. (e) Chini, M.; Crotti, P.; Macchia, F. J. Org. Chem. 1989, 54, 3930–3936.
34. (a) Subramanian, L. M.; Misra, G. S. Syn. Commun. 1984, 14, 1063–1065. (b) Gopalsamy, A.; Balasubramanian, K. K. Chem. Commun. 1988, 34–35. (c) Harvey, R. G.; Hahn, J. T.; Bukowska, M.; Jackson, H. J. Org. Chem. 1990, 55, 6161–6166.
35. (a) D-Barra, E.; Merino, S.; Verdfi, P. S.; Torres, J. Tetrahedron 1997, 53, 11437–11448. (b) Murakata, M.; Yasukata, T.; Aoki, T.; Nakajima, M.; Koga, K. Tetrahedron 1998, 54, 2449–2458. (c) Halterman, R. L.; Zhu, C. Tetrahedron Lett. 1999, 40, 7445–7448. (d) Goto, M.; Akimoto, K.; Aoki, K.; Shindo, M.; Koga, K. Tetrahedron Lett. 1999, 40, 8129–8132. (e) Cho, C. S.; Kim, B. T.; Kimb, T. J.; Shimb, S. C. Tetrahedron Lett. 2002, 43, 7987–7989. (f) Cid, J. M.; Romera, J. L.; Trabanco, A. A. Tetrahedron Lett. 2004, 45, 1133–1136. (g) Takahashi, T.; Nakao, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293–3308. (h) Cavallo, A. S.; Sedy, O.; Salisova, M.; Biba, M.; Welch, C. J.; Nafie´, L.; Freedmand, T. Tetrahedron: Asymmetry 2001, 12, 2703–2707. (i) Mahapatra, T.; Jana, N.; Nanda, S. Tetrahedron: Asymmetry 2008, 19, 1224–1232. (j) Eames, J.; Weerasooriya, N.; Coumbarides, G. S. Eur. J. Org. Chem. 2002, 181–187. (k) Inoue, Y.; Toyofuku, M.; Taguchi, M.; Okada, S.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1986, 59, 885–891. (l) Cho, C. S.; Kim, B. T.; Kim, T. J.; Shim, S. C. J. Org. Chem. 2001, 66, 9020–9022. (m) Crotti, P.; Bussolo, V. D.; Favero, L.; Pineschi, M. J. Org. Chem. 1996, 61, 9548–9552. (n) Rodriguez, A. L.; Bunlaksananusorn, T.; Knochel, P. Org. Lett. 2000, 2, 3285–3287.
36. (a) Hiroyuki, T.; Mutsuko, T.; Eietsu, H. J. Org. Chem. 2009, 74, 2467–2475. (b) Kobayashi, S.; Lam, W. W.-L.; Manabe, K. Tetrahedron Lett. 2000, 41, 6115–6120. (c) Thomas, P.; Vincent, D.; Francis, M.; Georges, D.; Sylvain, O.; Vincent, L. Angew. Chem. Int. Ed. Engl. 2007, 46, 7090–7093. (d) Faye, M.; Suzanne, T.; Frans, C.; Georges J, H. Eur. J. Org. Chem. 2004, 2707–2714. (e) Tao, Y. S.; Wang, B; Wang, B. M.; Qu, L.; Qu, J. P. Org. Lett. 2010, 12, 2726–2729. (f) Miura, T.; Shimada, M.; Murakami, M. Angew. Chem. Int. Ed. Engl. 2004, 44, 7598–7600.
37. 卓炳銓，一種新而有效的α-四氫酮α-烷基化反應之方法研究，民國九十八年(2009)國立中正大學化學暨生物化學學系大學部專題論文。
38. (a) Takeuchi, M.; Akiyama, R.; Kobayashi, S. J. Am. Chem. Soc. 2005, 127, 13096–13097. (b) Justribo, V.; Pellegrinet, S. C.; Colombo, M. I. J. Org. Chem. 2007, 72, 3702–3712. (c) Nakajima, M.; Yamamoto, S.; Yamaguchi, Y.; Nakamura, S.; Hashimoto, S. Tetrahedron 2003, 59, 7307–7314. (d) Kotsuki, H.; Arimura, K.; Ohishi, T.; Maruzasa, R. J. Org. Chem. 1999, 64, 3770–3773.
39. Kurdyumov, A. V.; Lin, N.; Hsung, R. P.; Gullickson, G. C.; Cole, K.
P.; Sydorenko, N.; Swidorski, J. J. Org. Lett. 2006, 8, 191–193.
40. (a) Chmielewski, M.; Jurczak, J. J. Org. Chem. 1981, 46, 2230–2233. (b) Thibonnet,
J.; Abarbri, M.; Parrain, J. L.; Ducheˆne, A. J. Org. Chem. 2002, 67, 3941–3944. (c) Zhu, X. F.; Schaffner, A. P.; Li, R. C.; Kwon, O. Org. Lett. 2005, 7, 2977–2980. (d) Uchiyama, M.; Ozawa, H.; Takuma, K.; Matsumoto, Y.; Yonehara, M.; Hiroya, K.; Sakamoto, T. Org. Lett. 2006, 8, 5517–5520. (e) Bellina, F.; Biagetti, M.; Carpita, A.; Rossi, R. Tetrahedron Lett. 2001, 42, 2859–2863. (f) Luigi Anastasia, L.; Xu, C.; Negishi, E. Tetrahedron Lett. 2002, 43, 5673–5676.
41. (a) Hon, Y. S.; Devulapally, R. Tetrahedron Lett. 2009, 50, 2831–2834. (b) Hon, Y. S.; Devulapally, R. Tetrahedron Lett. 2009, 50, 5713–5715.
42. Bowman, W. R.; Westlake, P. J. Tetrahedron 1992, 48, 4027–4038.
43. 吳佳芬，利用2-四氫酮合成苯并香豆素，民國九十九年(2010)國立中正大學化學暨生物化學學系碩士論文。
44. 趙邦媛，利用四氯化鈦促進2-聯芳香基-矽氧基乙醛進行Friedel-Crafts環化反應合成9-羥基菲衍生物，民國九十八年(2009)國立中正大學化學暨生物化學學系碩士論文。
45. Posakony, J.; Hirao, M.; Stevens, S.; Simon, J. A.; Bedalov, A. J. Med. Chem. 2004, 47, 2635–2644.
46. 麥正輝，新的一鍋化合成香豆素的方法開發，民國九十八年(2009) 國立中正大學化學暨生物化學學系大學部專題論文 與 同年行政院國科會補助大專學生參與專題研究計畫研究成果報告，及其後續研究。
47. (a) Tessier, P. E.; Nguyen, N.; Clay, M. D.; Fallis, A. G. Org. Lett. 2005, 7, 767–770. (b) McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1982, 24,979–982.
48. (a) Alami, M.; Ferri, F.; Linstrumelle, G. Tetrahedron Lett. 1993, 34, 6403–6406. (b) Gallagher, W. P.; Maleczka, R. E. J. Org. Chem. 2003, 68, 6775–6779.
49. (a) Hu, Y.; Li, C.; Kulkarni, B. A.; Strobel, G.; Lobkovsky, E.; Torczynski, R. M.; Porco, J. A., Jr. Org. Lett. 2001, 3, 1649–1652. (b) Tanaka, K.; Mori, K.; Yamamoto, M.; Katsumura, S. J. Org. Chem. 2001, 66, 3099–3110. (c) Li, C.; Porco, J. A., Jr J. Org. Chem. 2005, 70, 6053–6065. (d) Shoji, M.; Uno, T.; Kakeya, H.; Onose, R.; Shiina, I.; Osada, H.; Hayashi. Y. J. Org. Chem. 2005, 70, 9905–9915. (e) Li, C.; Porco, J. A., Jr J. Am. Chem. Soc. 2004, 126, 1310–1311. (f) Menz, H.; Kirsch, S. F. Org. Lett. 2008, 8, 4795–4797. (g) Panetta, J. A.; Rapoport, H. J. Org. Chem. 1982, 47, 946–950. (h) Fabio, R. D.; Bonadies, F. J. Org. Chem. 1984, 49, 1647–1649.
50. (a) Harvey, R. G.; Cortez, C.; Ananthanatayan, T. P.; Schmolka, S. J. Org. Chem. 1988, 53, 3936–3943. (b) Cheruku, S. R.; Padmanilayam, M. P.; Vennerstrom, J. L. Tetrahedron Lett. 2003, 44, 3701–3703.
51. (a) Yoshida, M.; Fujita, M.; Ishii, T.; Ihara, M. J. Am. Chem. Soc. 2003, 125, 4874–4881. (b) Marson, C. M.; Harper, S J. Org. Chem. 1998, 63, 9223–9231. (c) Paquette, L. A.; Andrea, L. B. J. Am. Chem. Soc. 1983, 105, 7352–7358. (d) Buzas, A.; Istrate, F.; Gagosz, F. Org. Lett. 2006, 8, 1957–1959.
52. Alcock, N. J.; Mann, I.; Peach, P.; Wills, M. Tetrahedron: Asymmetry 2002, 13, 2485–2490.
53. (a) Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537-4538. (b) Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
54. Backvall, J. E.; Plobeck, N. A. J. Org. Chem. 1990, 55, 4528–4531.
55. Bonadies, F.; Fabio, R. D.; Bonini, C. J. Org. Chem. 1984, 49, 1647–1649.
56. Highet, R. J.; Wildman, W. C. J. Am. Chem. Soc. 1955, 77, 4399–4401.
57. (a) Makoto, Y.; Yusuke, S.; Ikuya, S.; Akio, B. Synthesis 2005, 233–239.
(b) Robl, J. A.; Duncan, L. A.; Pluscec, J.; Karanewsky, D. S.; Gordon, E. M.; Ciosek, C. P.; Rich, L. C.; Dehmel, V. C.; Slusarchyk, D. A.; Harrity, T. W.; Obrien, K. A. J. Med. Chem. 1991, 34, 2804–2815. (c) Brown, D. S.; Marples, D. A.; Smith, P.; Walton, L. Tetrahedron 1995, 51, 3587–3606.
58. (a) Chow, Y. L.; Zhou, X. M.; Gaitan, T. J.; Wu, Z. Z. J. Am. Chem. Soc. 1989, 111, 3813–3818. (b) Badawy, D. S.; Kandeel, E. M.; Noha M. Awad, N. M.; Abdel-Rahman, H. Phosphorus, Sulfur and Silicon and the Related Elements, 2009, 184, 179–196. (c) Karimi, B.; Zareyee, D. Org. Lett. 2008, 10, 3989–3992. (d) Negishi, E. I.; Cope´ret, C.; Ma, S.; Mita, T.; Sugihara, T.; Tour, J. M. J. Am. Chem. Soc. 1996, 118, 5904–5918. (e) Dae, W. C.; Lee, H. Y.; Sun, W. O.; Jung, H. C.; Hea, J. P.; Mariano, P. S.; Ung, C. Y. J. Org. Chem. 2008, 73, 4539–4547. (f) Kouvarakisa, A.; Katerinopoulosa, H. E. Synth. Commun. 1995, 25, 3035–3044.