Total Synthesis of (+)-Macquarimicin A

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• 作者：Ryosuke Munakata ; Hironori Katakai ; Tatsuo Ueki ; Jun Kurosaka ; Ken-ichi Takao ; and Kin-ichi Tadano
• 刊名：Journal of the American Chemical Society
• 出版年：2003
• 出版时间：December 3, 2003
• 年：2003
• 卷：125
• 期：48
• 页码：14722 - 14723
• 全文大小：84K
• 年卷期：v.125,no.48(December 3, 2003)
• ISSN：1520-5126

文摘

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.