Tuesday, October 8, 2013

Stereoselective synthesis of (–)-lepadins A–C

by Mercedes Amat,* Alexandre Pinto, Rosa Griera and Joan Bosch 


A concise synthesis of the marine alkaloids (–)-lepadins A–C from a phenylglycinol-derived tricyclic lactam is reported. Key steps from the stereochemical standpoint involve stereoselective cyclocondensation, double bond hydrogenation, oxazolidine opening, hydroboration-oxidation, and Horner-Wadsworth-Emmons reactions.

Chemical Communications

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