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

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

48 Citations (Scopus)

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.

Original language	English
Pages (from-to)	14722-14723
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	125
Issue number	48
DOIs	https://doi.org/10.1021/ja038732p
Publication status	Published - 2003 Dec 3

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja038732p

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title = "Total Synthesis of (+)-Macquarimicin A",

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

AU - Ueki, Tatsuo

AU - Kurosaka, Jun

AU - Takao, Ken Ichi

AU - Tadano, Kin Ichi

PY - 2003/12/3

Y1 - 2003/12/3

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AB - 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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JF - Journal of the American Chemical Society

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Total Synthesis of (+)-Macquarimicin A

Abstract

ASJC Scopus subject areas

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