Total Synthesis of (+)-Macquarimicin A

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

Research output: Contribution to journalArticle

40 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 languageEnglish
Pages (from-to)14722-14723
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number48
DOIs
Publication statusPublished - 2003 Dec 3

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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    Munakata, R., Katakai, H., Ueki, T., Kurosaka, J., Takao, K. I., & Tadano, K. I. (2003). Total Synthesis of (+)-Macquarimicin A. Journal of the American Chemical Society, 125(48), 14722-14723. https://doi.org/10.1021/ja038732p