Total Synthesis of (+)-Macquarimicin A

Ryosuke Munakata, Hironori Katakai, Tatsuo Ueki, Jun Kurosaka, Ken Ichi Takao, Kin Ichi Tadano

研究成果: Article査読

40 被引用数 (Scopus)

抄録

The first total synthesis of (+)-macquarimicin A (1), a novel inhibitor of neutral sphingomyelinase (N-SMase) with antiinflammatory activity, has been accomplished. The present work determined the absolute configuration of (+)-1 and revised the C(2)?C(3) geometry to be Z. The synthesis features a transannular Diels?Alder reaction, which constructed the tetracyclic framework stereoselectively, and a convergent and efficient synthetic pathway, which afforded (+)-macquarimicin A (1) in 27 steps (longest linear sequence) with 9.9% overall yield.

本文言語English
ページ(範囲)14722-14723
ページ数2
ジャーナルJournal of the American Chemical Society
125
48
DOI
出版ステータスPublished - 2003 12 3

ASJC Scopus subject areas

  • 触媒
  • 化学 (全般)
  • 生化学
  • コロイド化学および表面化学

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