Concise photochemical synthesis of the antimalarial indole alkaloid decursivine

Mark Mascal; Kyle V. Modes; Asuman Durmus

doi:10.1002/anie.201006423

Concise photochemical synthesis of the antimalarial indole alkaloid decursivine

Mark Mascal, Kyle V. Modes, Asuman Durmus

Chemistry

Research output: Contribution to journal › Article › peer-review

50 Scopus citations

Abstract

A four-step synthesis of the extracyclic, antimalarial indole natural product decursivine is described starting from commercial piperonyl bromide and serotonin (see scheme). A photoinitiated reaction cascade involving indole radical cation formation, rearrangement, radical recombination, rearomatization, elimination, and diastereoselective auto-acid-catalyzed closure of the dihydrofuran ring combine in a single step to conclude this remarkably efficient synthesis.

Original language	English (US)
Pages (from-to)	4445-4446
Number of pages	2
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	19
DOIs	https://doi.org/10.1002/anie.201006423
State	Published - May 2 2011

Keywords

antimalarials
indoles
natural products
photochemistry
total synthesis

ASJC Scopus subject areas

Chemistry(all)
Catalysis

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AU - Modes, Kyle V.

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N2 - A four-step synthesis of the extracyclic, antimalarial indole natural product decursivine is described starting from commercial piperonyl bromide and serotonin (see scheme). A photoinitiated reaction cascade involving indole radical cation formation, rearrangement, radical recombination, rearomatization, elimination, and diastereoselective auto-acid-catalyzed closure of the dihydrofuran ring combine in a single step to conclude this remarkably efficient synthesis.

AB - A four-step synthesis of the extracyclic, antimalarial indole natural product decursivine is described starting from commercial piperonyl bromide and serotonin (see scheme). A photoinitiated reaction cascade involving indole radical cation formation, rearrangement, radical recombination, rearomatization, elimination, and diastereoselective auto-acid-catalyzed closure of the dihydrofuran ring combine in a single step to conclude this remarkably efficient synthesis.

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KW - indoles

KW - natural products

KW - photochemistry

KW - total synthesis

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SN - 1433-7851

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ER -

Concise photochemical synthesis of the antimalarial indole alkaloid decursivine

Abstract

Keywords

ASJC Scopus subject areas

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