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Differentiation of Nonconventional “Carbanions”—The Total Synthesis of Nemorosone and Clusianone
Author(s) -
Tsukano Chihiro,
Siegel Dionicio R.,
Danishefsky Samuel J.
Publication year - 2007
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.200703886
Subject(s) - carbanion , psychology , chemistry , stereochemistry
An unconventional approach : The total syntheses of nemorosone ( 1 ) and clusianone ( 2 ) have been achieved in a direct fashion through the generation and exploitation of nonconventional anions arising from a common intermediate ( 3 , see scheme). The key skeleton‐building stages are allylative de‐aromatization and iodinative cyclization. These acylphloroglucinol natural products display promising cytotoxic and anti‐HIV activity, respectively.