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Total Synthesis of a Protected Aglycon of the Kedarcidin Chromophore
Author(s) -
Ogawa Kouki,
Koyama Yasuhito,
Ohashi Isao,
Sato Itaru,
Hirama Masahiro
Publication year - 2009
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.200805518
Subject(s) - chromophore , amide , ring (chemistry) , chemistry , stereochemistry , epoxide , convergent synthesis , combinatorial chemistry , total synthesis , organic chemistry , catalysis
Strong support for the recently proposed structure of the kedarcidin chromophore has been obtained through the convergent synthesis of the aglycon. The key features of the synthesis are an efficient assembly of the four fragments, a novel strategy involving an alkynyl epoxide, a cerium amide promoted nine‐membered diyne ring cyclization, and a SmI 2 ‐mediated reductive 1,2‐elimination. TBS= tert ‐butyldimethylsilyl, MOM=methoxymethyl.