title: Study on the biosynthesis of the notoamides: Pinacol-type rearrangement of the isoprenyl unit in deoxybrevianamide E and 6-hydroxydeoxybrevianamide E.
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.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto, 862-0973, Japan.
authors.forename: Hikaru
authors.initials: H
authors.lastname: Kato
authors.forename: Yuichi
authors.initials: Y
authors.lastname: Nakamura
authors.forename: Jennifer M
authors.initials: JM
authors.lastname: Finefield
authors.forename: Hideharu
authors.initials: H
authors.lastname: Umaoka
authors.forename: Takashi
authors.initials: T
authors.lastname: Nakahara
authors.forename: Robert M
authors.initials: RM
authors.lastname: Williams
authors.forename: Sachiko
authors.initials: S
authors.lastname: Tsukamoto