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- Title
Carboalumination-Epoxide Ring Opening for the Formation of 1,4-Disubstituted ( Z)-3,6-Alkadienols.
- Authors
Zhang, Quan; Jing, Yuhuan; Myles, David C.; Li, Yong; Chen, Yue
- Abstract
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).
- Subjects
ALKENYLATION; ALKYNES; EPOXY compounds; HYDROCARBONS; ALUMINUM compounds
- Publication
Chinese Journal of Chemistry, 2013, Vol 31, Issue 6, p773
- ISSN
1001-604X
- Publication type
Article
- DOI
10.1002/cjoc.201300235