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  • Title: Synthesis of the bis-spiroacetal moiety of spirolides B and D.
    Author: Meilert K, Brimble MA.
    Journal: Org Lett; 2005 Aug 04; 7(16):3497-500. PubMed ID: 16048326.
    Abstract:
    An enantioselective synthesis of the bis-spiroacetal fragment of spirolides B and D is reported. The carbon framework was constructed via Barbier reaction of dihydropyran 3 with aldehyde 4, followed by a double oxidative radical cyclization to construct the bis-spiroacetal. A silyl-modified Prins cyclization and enantioselective crotylation successfully installed the stereocenters in the cyclization precursor. The initial unsaturated bis-spiroacetals 2a-d underwent equilibration during epoxidation to trans-epoxide 14 that was converted to a tertiary alcohol. [reaction: see text]
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