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Bioinspired chemical synthesis of monomeric and dimeric stephacidin A congeners.


ABSTRACT: Stephacidin A and its congeners are a collection of secondary metabolites that possess intriguing structural motifs. They stem from unusual biosynthetic sequences that lead to the incorporation of a prenyl or reverse-prenyl group into a bicyclo[2.2.2]diazaoctane framework, a chromene unit or the vestige thereof. To complement biosynthetic studies, which normally play a significant role in unveiling the biosynthetic pathways of natural products, here we demonstrate that chemical synthesis can provide important insights into biosynthesis. We identify a short total synthesis of congeners in the reverse-prenylated indole alkaloid family related to stephacidin A by taking advantage of a direct indole C6 halogenation of the related ketopremalbrancheamide. This novel strategic approach has now made possible the syntheses of several natural products, including malbrancheamides B and C, notoamides F, I and R, aspergamide B, and waikialoid A, which is a heterodimer of avrainvillamide and aspergamide B. Our approach to the preparation of these prenylated and reverse-prenylated indole alkaloids is bioinspired, and may also inform the as-yet undetermined biosynthesis of several congeners.

SUBMITTER: Mukai K 

PROVIDER: S-EPMC6317722 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

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Bioinspired chemical synthesis of monomeric and dimeric stephacidin A congeners.

Mukai Ken K   de Sant'Ana Danilo Pereira DP   Hirooka Yasuo Y   Mercado-Marin Eduardo V EV   Stephens David E DE   Kou Kevin G M KGM   Richter Sven C SC   Kelley Naomi N   Sarpong Richmond R  

Nature chemistry 20170918 1


Stephacidin A and its congeners are a collection of secondary metabolites that possess intriguing structural motifs. They stem from unusual biosynthetic sequences that lead to the incorporation of a prenyl or reverse-prenyl group into a bicyclo[2.2.2]diazaoctane framework, a chromene unit or the vestige thereof. To complement biosynthetic studies, which normally play a significant role in unveiling the biosynthetic pathways of natural products, here we demonstrate that chemical synthesis can pro  ...[more]

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