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J Org Chem ; 78(21): 10588-95, 2013 Nov 01.
Article in English | MEDLINE | ID: mdl-24079664

ABSTRACT

A highly convergent and stereocontrolled synthesis of epothilone D (4) is reported. Key features are a cheap and Z-selective synthesis of the northern half based on nerol and acetoacetate and chromium(II)-mediated Reformatsky reactions as a powerful tool for chemoselective asymmetric carbon-carbon bond formations, including an unusual stereospecific macroaldolization.


Subject(s)
Aldehydes/chemistry , Epothilones/chemical synthesis , Macrolides/chemical synthesis , Chromium/chemistry , Epothilones/chemistry , Macrolides/chemistry
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