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Carboalumination‐Epoxide Ring Opening for the Formation of 1,4‐Disubstituted ( Z )‐3,6‐Alkadienols
Author(s) -
Zhang Quan,
Jing Yuhuan,
Myles David C.,
Li Yong,
Chen Yue
Publication year - 2013
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201300235
Subject(s) - chemistry , epoxide , negishi coupling , ring (chemistry) , stereochemistry , combinatorial chemistry , epothilone , medicinal chemistry , organic chemistry , catalysis
Allylalumination of alkynes ( i.e . forming Negishi's ( Z )‐alkenyl dialkylalane) followed by alkenylation of epoxides provides 1,4‐disubstituted ( Z )‐3,6‐alkadienols. The alkenylation can be facilitated by the presence of a neighbouring coordinating group in the epoxides. This "one‐pot" approach has been successfully applied in the large‐scale production of C10–C15 fragment of 9,10‐didehydroepothilone D (a synthetic epothilone analog as an anti‐cancer agent in phase 2 clinical trials).
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