Total Synthesis of (+)-Macquarimicin A

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

Research output: Contribution to journalArticle

38 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

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Sphingomyelin Phosphodiesterase
Anti-Inflammatory Agents
Geometry
macquarimicin A

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Munakata, R., Katakai, H., Ueki, T., Kurosaka, J., Takao, K., & 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

Total Synthesis of (+)-Macquarimicin A. / Munakata, Ryosuke; Katakai, Hironori; Ueki, Tatsuo; Kurosaka, Jun; Takao, Kenichi; Tadano, Kin Ichi.

In: Journal of the American Chemical Society, Vol. 125, No. 48, 03.12.2003, p. 14722-14723.

Research output: Contribution to journalArticle

Munakata, R, Katakai, H, Ueki, T, Kurosaka, J, Takao, K & Tadano, KI 2003, 'Total Synthesis of (+)-Macquarimicin A', Journal of the American Chemical Society, vol. 125, no. 48, pp. 14722-14723. https://doi.org/10.1021/ja038732p
Munakata R, Katakai H, Ueki T, Kurosaka J, Takao K, Tadano KI. Total Synthesis of (+)-Macquarimicin A. Journal of the American Chemical Society. 2003 Dec 3;125(48):14722-14723. https://doi.org/10.1021/ja038732p
Munakata, Ryosuke ; Katakai, Hironori ; Ueki, Tatsuo ; Kurosaka, Jun ; Takao, Kenichi ; Tadano, Kin Ichi. / Total Synthesis of (+)-Macquarimicin A. In: Journal of the American Chemical Society. 2003 ; Vol. 125, No. 48. pp. 14722-14723.
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