Formal synthesis of optically active ingenol via ring-closing olefin metathesis

Kazushi Watanabe, Yuto Suzuki, Kenta Aoki, Akira Sakakura, Kiyotake Suenaga, Hideo Kigoshi

研究成果: Article査読

45 被引用数 (Scopus)

抄録

The construction of strained carbon skeletons by ring-closing olefin metathesis (RCM) was investigated. With well-designed diene 4, RCM was found to be applicable to the formation of a highly strained inside-outside bicyclo[4.4.1]undecane skeleton of ingenol, a bioactive diterpenoid, and formal total synthesis of optically active ingenol (1) was achieved. The key features of this synthesis are construction of an A-ring by spirocyclization of the ketone with an allylic chloride unit, 26, and ring closure of a B-ring by olefin metathesis. Starting from Funk's keto ester 6, the key intermediate aldehyde 9 in Winkler's total synthesis was synthesized in eight steps in 12.5% overall yield. This strategy of direct cyclization of a strained inside-outside skeleton provided the first easy access to optically active ingenol.

本文言語English
ページ(範囲)7802-7808
ページ数7
ジャーナルJournal of Organic Chemistry
69
23
DOI
出版ステータスPublished - 2004 11 12
外部発表はい

ASJC Scopus subject areas

  • 有機化学

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