Total Synthesis of (+)‐Machaeriol D with a Key Regio‐ and Stereoselective S N 2′ Reaction | Zendy

Wang Qiaoling | Zendy; Huang Qinggang | Zendy; Chen Bo | Zendy; Lu Jiangping | Zendy; Wang Hui | Zendy; She Xuegong | Zendy; Pan Xinfu | Zendy

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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.

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