Synthesis of a Lactone Diastereomer of the Cembranolide Uprolide D
2010
A convergent stereoselective synthesis of a C1/C14 bis-epimer of uprolide D is described in which an intramolecular Barbier-type reaction was employed for macrocyclization with concomitant introduction of the C1 and C14 stereocenters of a fused α-methylene lactone ring through an anti-Felkin−Anh transition state. Unlike previous examples of allyl chromium additions, none of the Felkin−Anh derived adduct could be detected.
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