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  • Title: Total synthesis of methyl sarcophytoate, a marine natural biscembranoid.
    Author: Ichige T, Okano Y, Kanoh N, Nakata M.
    Journal: J Org Chem; 2009 Jan 02; 74(1):230-43. PubMed ID: 19053598.
    Abstract:
    The total synthesis of methyl sarcophytoate (1), a marine natural biscembranoid, has been achieved by the thermal Diels-Alder reaction between the 14-membered dienophile unit, methyl sarcoate (2), and the 14-membered diene unit 64. Methyl sarcoate (2) was prepared using n-BuLi-Bu(2)Mg-mediated dithiane coupling, Kosugi-Migita-Stille coupling, and Grubbs ring-closing metathesis. The diene unit 64 was prepared using Sharpless asymmetric epoxidation, Grubbs ring-closing metathesis, 6-exo-tet epoxide opening, and n-BuLi-Bu(2)Mg-mediated Ito-Kodama cyclization. The final Diels-Alder reaction between 2 and 64 proceeded with high site, endo/exo, pi-face, and regioselectivities. During this reaction, partial E --> Z isomerization at the C4 position was observed.
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