Synthesis of the Polyketide (E)-Olefin of the Jamaicamides

Abstract

The jamaicamides, isolated in Jamaica from the cyanobacterium Lyngbya majuscula, are new mixed polyketide-peptides that are known to be sodium channel blockers. The polyketide moiety contains an (E)-vinyl chloride, an undetermined methyl stereocenter (C9), and an (E)-olefin. Herein, we report the synthesis of the (E)-olefin moiety of the polyketide of the jamaicamides utilizing a Kocienski–Julia coupling.

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GRAPHICAL ABSTRACT

Keywords:

• Jamaicamides
• Kocienski–Julia coupling
• marine natural products
• polyketide

ACKNOWLEDGMENTS

This work was supported in part by a Grant-in-Aid for Young Scientists (B) from the Ministry of Education, Culture, Sports, Science, and Technology (MEXT) of Japan. A fellowship from Yoshida Scholarship Foundation (to Satoshi Watanabe) is gratefully acknowledged.