Premium
Total Synthesis of (+)‐Machaeriol D with a Key Regio‐ and Stereoselective S N 2′ Reaction
Author(s) -
Wang Qiaoling,
Huang Qinggang,
Chen Bo,
Lu Jiangping,
Wang Hui,
She Xuegong,
Pan Xinfu
Publication year - 2006
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.200600006
Subject(s) - stereoselectivity , stereocenter , enantioselective synthesis , chemistry , sn2 reaction , stereochemistry , natural product , combinatorial chemistry , organic chemistry , catalysis
A general strategy for the synthesis of hexahydrodibenzopyrans (HHDBPs) is illustrated in the enantioselective total synthesis of (+)‐machaeriol D. In the key step, an S N 2′ reaction of an aryl cyanocuprate with a silyl enol ether of an optically active α,β‐epoxycyclohexanone enabled the construction of the four stereocenters of the natural product with high regio‐ and stereoselectivity (see scheme; R=methoxymethyl). TMS=trimethylsilyl, TBS= tert ‐butyldimethylsilyl.