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  • Title: Total synthesis of (-)-bitungolide F and determination of its absolute stereochemistry.
    Author: Ghosh S, Kumar SU, Shashidhar J.
    Journal: J Org Chem; 2008 Feb 15; 73(4):1582-5. PubMed ID: 18201100.
    Abstract:
    A highly convergent total synthesis of bitungolide F leading to the assignment of its absolute stereochemistry is described. The key steps include a Horner-Wadsworth-Emmons olefination to construct the C7-C8 bond, a Wittig reaction to introduce the conjugate E,E-olefinic moiety in the molecule, and finally a ring-closing metathesis reaction to construct the six-membered alpha,beta-unsaturated delta-lactone of the molecule. Modified Evans's syn-aldol reaction, using Crimmins's protocol, was used to install the stereochemistries at the C4 and C5 centers. The stereochemistry at C9 was introduced by means of hydroxy-directed reduction of the C9 keto using Evans's protocol.
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