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Total Synthesis of the Chlorine‐Containing Hapalindoles K, A, and G
Author(s) -
Chandra Aroop,
Johnston Jeffrey N.
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.201100957
Subject(s) - chemistry , stereoselectivity , chlorine , indole test , electrophilic substitution , cycloaddition , electrophile , total synthesis , medicinal chemistry , intermolecular force , chloride , dehydration , organic chemistry , stereochemistry , catalysis , molecule , biochemistry
A common approach : Overall brevity in the synthesis of the title compounds (see scheme) is achieved by a sequential electrophilic aromatic substitution of indole and a regio‐ and diastereoselective intermolecular Diels–Alder cycloaddition to establish the key precursor—a neopentyl chloride. A stereoselective Ritter reaction and dehydration are used for the installation of the isonitrile unit.