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Enantioselective Total Synthesis of Macrolide Antitumor Agent (−)-Lasonolide A

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journal contribution
posted on 12.04.2007, 00:00 authored by Arun K. Ghosh, Gangli Gong
An enantioselective total synthesis of (−)-lasonolide A is described. The upper tetrahydropyran ring was constructed stereoselectively by an intramolecular 1,3-dipolar cycloaddition reaction. The bicyclic isooxazoline led to the tetrahydropyran ring as well as the quaternary stereocenter present in the molecule. The lower tetrahydropyran ring was assembled by a catalytic asymmetric hetero-Diels−Alder reaction as the key step. Three stereocenters were enantioselectively installed in this single step reaction.

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