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Concise Photochemical Synthesis of the Antimalarial Indole Alkaloid Decursivine
Author(s) -
Mascal Mark,
Modes Kyle V.,
Durmus Asuman
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201006423
Subject(s) - indole test , chemistry , indole alkaloid , ring (chemistry) , indoline , cascade , total synthesis , combinatorial chemistry , bromide , radical cyclization , closure (psychology) , stereochemistry , medicinal chemistry , organic chemistry , chromatography , economics , market economy
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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