Tetrahedron

Efficient synthesis of the key intermediate triptophenolide methyl ether for the synthesis of (−)-triptolide

B Zhou, X Li, H Feng, Y Li

Index: Zhou, Bing; Li, Xiaomei; Feng, Huijin; Li, Yuanchao Tetrahedron, 2010 , vol. 66, # 29 p. 5396 - 5401

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Citation Number: 16

Abstract

An efficient synthesis of triptophenolide methyl ether 4 from the readily available abietic acid 3 in nine steps is described and successfully applied to the synthesis of (−)-triptolide 1. The route is of characteristic of low cost, high yield and easy operation. In addition, every reaction in this route has been successfully scaled-up to a 100g substrate level without loss of yield.

~69%

~96%

~99%

Semisynthesis of C-ring modified triptolide analogues and th...

[Aoyagi, Yutaka; Hitotsuyanagi, Yukio; Hasuda, Tomoyo; Fukaya, Haruhiko; Takeya, Koichi; Aiyama, Ritsuo; Matsuzaki, Takeshi; Hashimoto, Shusuke Bioorganic and Medicinal Chemistry Letters, 2006 , vol. 16, # 7 p. 1947 - 1949]

Total synthesis of l-triptonide and l-triptolide

[Tamelen, E. E. van; Demers, J. P.; Taylor, E. G.; Koller, K. Journal of the American Chemical Society, 1980 , vol. 102, # 16 p. 5424 - 5425]