A biomimetic approach to taxol: Stereoselective synthesis of a 12-membered ring ene-epoxide

Takashi Takahashi, Tadashi Okabe, Hajime Iwamoto, Yoichiro Hirose, Haruo Yamada, Takayuki Doi, Shuji Usui, Yoshimasa Fukazawa

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1 Citation (Scopus)

Abstract

The stereoselective synthesis of a taxol intermediate via a biomimetic route is described. Aldol condensation of γ-butyrolactone and citral derivatives generated three stereogenic centers at positions C1, C2, and C11 corresponding to taxol. Intramolecular alkylation of the cyanohydrin ether efficiently formed the 12-membered ring system in which stereoselective reduction, followed by directed epoxidation, afforded the key intermediate epoxide.

Original languageEnglish
Pages (from-to)31-37
Number of pages7
JournalIsrael Journal of Chemistry
Volume37
Issue number1
DOIs
Publication statusPublished - 1997 Jan 1
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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    Takahashi, T., Okabe, T., Iwamoto, H., Hirose, Y., Yamada, H., Doi, T., Usui, S., & Fukazawa, Y. (1997). A biomimetic approach to taxol: Stereoselective synthesis of a 12-membered ring ene-epoxide. Israel Journal of Chemistry, 37(1), 31-37. https://doi.org/10.1002/ijch.199700006