American Chemical Society
ol201283n_si_001.pdf (2.07 MB)

A Concise Asymmetric Total Synthesis of (+)-Brevisamide

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journal contribution
posted on 2011-07-15, 00:00 authored by Aaron T. Herrmann, Steven R. Martinez, Armen Zakarian
A new protecting-group-free synthesis of the marine monocyclic ether (+)-brevisamide is reported. The enantioselective synthesis utilizes a key asymmetric Henry reaction and an Achmatowicz rearrangement for the formation of the tetrahydropyran ring. A penultimate Stille cross-coupling allows for an efficient installation of the conjugated (E,E)-diene side chain ultimately delivering (+)-brevisamide.