Total synthesis of (+)-macquarimicin A

  • J Am Chem Soc. 2003 Dec 3;125(48):14722-3. doi: 10.1021/ja038732p.
Ryosuke Munakata  1 ,  Hironori Katakai ,  Tatsuo Ueki ,  Jun Kurosaka ,  Ken-ichi Takao ,  Kin-ichi Tadano
Affiliations
  • 1. Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
PMID: 14640644 DOI: 10.1021/ja038732p
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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