Total Synthesis of (+)-Macquarimicin A

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

doi:10.1021/ja038732p

Total Synthesis of (+)-Macquarimicin A

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

応用化学科

研究成果: Article › 査読

41 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
巻	125
号	48
DOI	https://doi.org/10.1021/ja038732p
出版ステータス	Published - 2003 12月 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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abstract = "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.",

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AU - Munakata, Ryosuke

AU - Katakai, Hironori

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AU - Takao, Ken Ichi

AU - Tadano, Kin Ichi

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Total Synthesis of (+)-Macquarimicin A

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