本實驗室所進行之雙帖類天然物─紫杉醇的合成計畫中，合成的策略為：先分別進行A環和C環前驅物的合成，然後再將兩環結合構成B環，藉此完成紫杉醇的主要中心結構。
此篇論文的主要研究內容，乃在探討紫杉醇C環前驅物的合成。利用逆推合成分析法，合理的推論合成路徑，達到期望的目的產物。
首先，以2-夫喃酸（I）為起始物，經過酯化、溴化、水解及脫羧反應後得到化合物（II）；在經過甲基化、甲醯基化、甲醯基保護及甲氧基化反應得到化合物（III）17,18；藉由去保護、還原後與乙烯氰做Diels-Alder反應後得到化合物（IV）；經過水解、羰基保護、還原、開環、醇基保護後得到化合物（V）；接著還原、溴化後與1,3-二硫代環己烷反應得到鹽類（VI）；隨後利用3,3-sigmatropic rearrangement即可得到最終紫杉醇C環的前驅物A。

The strategy used in our laboratory to synthesize diterpene natural compound-Taxol is that by synthesizing ring A and ring C with latent functions separately, followed by the coupling of ring A and ring C to form ring B and succeed the construction of the back bond structure of the target molecule. Together with the elaboration of the necessary functional groups with the correct stereochemistry the Taxol molecule could then be synthesized.
This dissertation describes the preparation of Ring C intermidiate which will be used in the total synthesis of Taxol. We inferred the reasonable strategy to get the target by retrosynthetic analysis.
Firstly, the starting material, 2-furoic acid was converted, by way of esterification, bromination, hydrolysis and decarboxylation into compound (II). After methylation, formylation, formyl group protection and methoxylation, the compound (III)17,18 was obtained. Followed by hydrolysis, reduction and the Diels-Alder reaction with acrylonitrile, the compound (IV) was formed. By way of hydrolysis, protection of carbonyl group, ring openning and hydroxyl group protection, the compound (V) was otained. Followed by reduction, bormination and reaction with 1,3-dithian, a sulfonium salt compound (VI) was formed. Finally, the Ring C intermidiate will be obtained by 3,3-sigmatropic rearrangement.

中文摘要………………………………I
英文摘要………………………………II
謝誌……………………………………IV
目錄………………………………………V
附錄一……………………………………VI
圖譜資料
第一章 緒 論……………………………1
1-1紫杉醇的來源與簡介………………1
1-2紫杉醇的療效………………………4
1-3合成紫杉醇不同路徑之探討………6
1-4紫杉醇C環中間物之合成研究……10
第二章 結果與討論…………………13
2-1紫杉醇C環中間產物的合成………13
2-2關鍵步驟-開環的探討……………29
第三章 實 驗……………………………34
3-1實驗試劑……………………………34
3-2實驗儀器……………………………36
3-3實驗步驟……………………………38
附錄二……………………………………82
參考文獻

1.(a)李文權, 科學月刊, 1994, 25, 490.
(b)汪嘉林, 科學月刊, 1994, 25, 495.
(c)何子樂, 科學月刊, 1997, 28, 283.
2.(a)王緯書, 抗癌新藥：太平洋紫杉醇,
http://www1.vghtpe.got.tw/vghtpe
(b)黃文豐, Taxol 96小時注射及口服Estramustine phosphate
治療轉移性、頑固性攝護腺癌(臨床第二期試驗)
http://www1.vghtpe.got.tw/vghtpe
(c)趙偉婷, Paclitalel用於有重大危險因子的婦科癌症病人
http://www1.vghtpe.got.tw/vghtpe
(d) 陶聲洋防癌基金會, 認識癌症,
http://tis.mc.ntu.edu.tw/~dao/icon3.htm
3. Matthew Lerner. Chemical Market Reporter 1997, 251, 4.
4. Lee Makowski. UniSci Science and Research News 12-Jan- 1999.
5. Horwitz, S. B; Fant, J; Schiff, P. B. Proc. Natl.cad.Sci.
USA 1980, 77, 1561.
6. Horwitz, S. B; Fant, J; Schiff, P. B. Nature 1979, 277, 665.
7. Nicolaou, K. C;Sorensen, E, J. CLASSICS IN TOTAL SYNTHESIS
1996, 655.
8.(a)Nicolaou, K. C.; Nantermet, P. G.;Ueno, H.;Guy, R.
K.; Couladouros, E. A.;Sorensen, E. J. J. Am. Chem.
Soc. 1995, 117, 624.
(b)Nicolaou, K. C.; Liu, J. J.; Yang, Z.; Ueno,H.;Sorensen,
E. J.; Claiborne, C. F.;Guy, R. K.;Hwang, C. K.;Nakada,
M.; Nantermet, P. G. J. Am. Chem. Soc. 1995, 117, 634.
(c)Nicolaou, K. C.; Yang, Z.; Liu, J. J.; Nantermet, P.
G. ; Claiborne, C. F.; Renand, J.; Guy,R. K.;Shibayama,
K. J. Am. Chem. Soc. 1995, 117, 645.
(d)Nicolaou, K. C.; Ueno, H.; Liu, J. J.; Nantermet, P.
G. ; Yang, Z.; Renand, J.;Daulvannan, K.; Chadha, R. J.
J. Am. Chem. Soc. 1995, 117, 653.
9.Di Grandi, M. J.; Coburn, C. A.; Isaacs, R. C. A.;
Danishefsky, S. J. J. Org. Chem. 1993, 58, 7728.
10.Danishefsky, S. J.; Masters, J. J.; Young, W. B.;
Link, J. T.; Snyder, L. B.; Magee, T. V.; Jung, D. K.;
Isaacs, R. C. A,; Bornmann, W. G.; Alaimo, C. A.;
Coburn, C. A.; Di Grandi, M. J. J. Am. Chem. Soc.
1996, 118, 2843.
11.Jesús Avila Life Science 1992, 50, 327.
12.Wani, M. C.; Wall, M. E.; Taylor, H. L. J. Am. Chem. Soc.
1971, 93, 2325.
13.Holmes, F. A.; Walters, R. S.; Theriault, R. L.; Forman,
A. D.; Newton, L. K.; Raber, M. N.; Buzdar, A. U.; Frye,
D. K.; Hortobagyi, G. N. J. Natl.Cancer Inst. 1991, 83,
1797.
14.Montaigen, M. D. FITOTERAPIA 1993, LXIV, 5.
15.Elaine Blume J. Natl.Cancer Inst. 1992, 84, 1464.
16.Bormamn, s. C&E News 1991, Setpember 2, 11.
17.魯啟慧, 紫杉醇C環之合成研究, 碩士論文, 私立中原大學化學
研究所, 1996.