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

研究成果: Article

1 引用 (Scopus)

抜粋

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.

元の言語English
ページ(範囲)31-37
ページ数7
ジャーナルIsrael Journal of Chemistry
37
発行部数1
DOI
出版物ステータスPublished - 1997 1 1
外部発表Yes

ASJC Scopus subject areas

  • Chemistry(all)

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  • これを引用

    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