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  • Title: Total synthesis of (+)-macquarimicin A.
    Author: Munakata R, Katakai H, Ueki T, Kurosaka J, Takao K, Tadano K.
    Journal: J Am Chem Soc; 2003 Dec 03; 125(48):14722-3. PubMed ID: 14640644.
    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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