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Total Synthesis of (+)-Macquarimicin A

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posted on 03.12.2003, 00:00 by Ryosuke Munakata, Hironori Katakai, Tatsuo Ueki, Jun Kurosaka, Ken-ichi Takao, Kin-ichi Tadano
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.