Study on the biosynthesis of the notoamides: Pinacol-type rearrangement of the isoprenyl unit in deoxybrevianamide E and 6-hydroxydeoxybrevianamide E

  • Tetrahedron Lett. 2011 Dec 21;52(51):6923-6926. doi: 10.1016/j.tetlet.2011.10.065.
Hikaru Kato  1 ,  Yuichi Nakamura ,  Jennifer M Finefield ,  Hideharu Umaoka ,  Takashi Nakahara ,  Robert M Williams ,  Sachiko Tsukamoto
Affiliations
  • 1. Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto, 862-0973, Japan.
PMID: 22140281 DOI: 10.1016/j.tetlet.2011.10.065
Abstract

Two reverse-prenylated Indole Alkaloids, deoxybrevianamide E and 6-hydroxydeoxybrevianamide E, are proposed as biosynthetic precursors for advanced metabolites isolated from the marine-derived Aspergillus sp. In order to uncover the role of the Alkaloids in the biosynthetic pathway, the feeding experiments of the [(13)C](2)-[(15)N]-labeled deoxybrevianamide E and 6-hydroxydeoxybrevianamide E were performed to afford the metabolites, which were produced by oxidation and successive pinacol-type rearrangement of the isoprenyl units.

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