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A Convenient C-H Functionalization Platform for Pyrroloiminoquinone Alkaloid Synthesis.

ABSTRACT: Pyrroloiminoquinone alkaloids represent a structurally intriguing class of natural products that display an array of useful biological properties. Here, we present a versatile and scalable platform for the synthesis of this diverse family - and in particular the antitumor discorhabdins - built upon sequential selective C-H functionalization of tryptamine. The utility of this strategy is showcased through short formal syntheses of damirones A-C, makaluvamines D and I, and discorhadbin E. Additionally, we describe efforts to develop the first catalytic asymmetric entry to the discorhabdin subclass.

SUBMITTER: Smith MW

PROVIDER: S-EPMC6937132 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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A Convenient C-H Functionalization Platform for Pyrroloiminoquinone Alkaloid Synthesis.

Smith Myles W MW Falk Isaac D ID Ikemoto Hideya H Burns Noah Z NZ

Tetrahedron 20190508 24

Pyrroloiminoquinone alkaloids represent a structurally intriguing class of natural products that display an array of useful biological properties. Here, we present a versatile and scalable platform for the synthesis of this diverse family - and in particular the antitumor discorhabdins - built upon sequential selective C-H functionalization of tryptamine. The utility of this strategy is showcased through short formal syntheses of damirones A-C, makaluvamines D and I, and discorhadbin E. Addition ...[more]

PMID: 31889735

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