Total synthesis of epothilone D: the nerol/macroaldolization approach.

The Journal of organic chemistry (2013-10-02)
Ludger A Wessjohann, Günther O Scheid, Uwe Eichelberger, Sumaira Umbreen
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
cis-3,7-Dimethyl-2,6-octadien-1-ol, 97%