Unified Total Synthesis of (−)-Enigmazole A and (−)-15-O-Methylenigmazole A

Keisuke Sakurai, Keita Sakamoto, Makoto Sasaki, Haruhiko Fuwa

研究成果: Article査読

5 被引用数 (Scopus)

抄録

The total synthesis of cytotoxic marine phosphomacrolides, (−)-enigmazole A and (−)-15-O-methylenigmazole A, is described in detail. The 2,6-cis-substituted tetrahydropyran ring was efficiently elaborated by using a tandem olefin cross-metathesis/intramolecular oxa-Michael addition reaction. The 18-membered macrolactone skeleton was forged via a Au-catalyzed propargylic benzoate rearrangement/macrocyclic ring-closing metathesis sequence. Late-stage diversification of a common intermediate enabled unified total synthesis of (−)-enigmazole A and (−)-15-O-methylenigmazole A.

本文言語English
ページ(範囲)3494-3502
ページ数9
ジャーナルChemistry - An Asian Journal
15
21
DOI
出版ステータスPublished - 2020 11月 2

ASJC Scopus subject areas

  • 生化学
  • 有機化学

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