Bravo for Brevisamide

Bravo for Brevisamide

Author: David Bradley

There is an abundance of natural products to be studied from marine organisms, many of which have novel physiological properties that translate into antibiotic, anticancer, anti-inflammatory, and other activities of interest to medicinal chemists. However, many of these substances are complex and offer numerous challenges for synthetic chemists.

One such compound, (–)-brevisamide (pictured), a toxin from the “red tide” dinoflagellate Karenia brevis, provides a potential model for how fused polyethers are biosynthesized. Researchers at the University of Hyderabad, India, and their colleagues at the CSIR-Indian Institute of Chemical Technology, Hyderabad, have devised a formal stereoselective synthesis of the monocyclic ether alkaloid (–)-brevisamide. The team worked their way through a series of synthetic trials to come up with a reaction scheme involving a syn-Aldol reaction, Sharpless asymmetric epoxidation, and stereoselective construction of a tetrahydropyran ring by 6-endo-cyclization of a substituted hydroxy styrylepoxide.

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