Literature DB >> 21678904

A concise asymmetric total synthesis of (+)-brevisamide.

Aaron T Herrmann1, Steven R Martinez, Armen Zakarian.   

Abstract

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.
© 2011 American Chemical Society

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Year:  2011        PMID： 21678904      PMCID： PMC3365585          DOI： 10.1021/ol201283n

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  26 in total

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8.  An asymmetric total synthesis of brevisamide.

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Review 3.  Chemodiversity of Brevetoxins and Other Potentially Toxic Metabolites Produced by Karenia spp. and Their Metabolic Products in Marine Organisms.

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