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

56 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

Access to Document

10.1002/anie.201006423

Cite this

@article{8771495fbc0945799f3095dd75d1face,

title = "Concise photochemical synthesis of the antimalarial indole alkaloid decursivine",

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.",

keywords = "antimalarials, indoles, natural products, photochemistry, total synthesis",

author = "Mark Mascal and Modes, {Kyle V.} and Asuman Durmus",

year = "2011",

month = may,

day = "2",

doi = "10.1002/anie.201006423",

language = "English (US)",

volume = "50",

pages = "4445--4446",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "19",

}

TY - JOUR

T1 - Concise photochemical synthesis of the antimalarial indole alkaloid decursivine

AU - Mascal, Mark

AU - Modes, Kyle V.

AU - Durmus, Asuman

PY - 2011/5/2

Y1 - 2011/5/2

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.

KW - antimalarials

KW - indoles

KW - natural products

KW - photochemistry

KW - total synthesis

UR - http://www.scopus.com/inward/record.url?scp=79955488322&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79955488322&partnerID=8YFLogxK

U2 - 10.1002/anie.201006423

DO - 10.1002/anie.201006423

M3 - Article

C2 - 21480441

AN - SCOPUS:79955488322

VL - 50

SP - 4445

EP - 4446

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 19

ER -

Concise photochemical synthesis of the antimalarial indole alkaloid decursivine

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this