Total synthesis of epothilone D: the nerol/macroaldolization approach.
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.
Department of Bioorganic Chemistry, Leibniz-Institute of Plant Biochemistry , Weinberg 3, D-06120 Halle (Saale), Germany.
Ludger A
LA
Wessjohann
Günther O
GO
Scheid
Uwe
U
Eichelberger
Sumaira
S
Umbreen
D000447:Aldehydes / Q000737:chemistry*; D002857:Chromium / Q000737:chemistry; D034261:Epothilones / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry
D000447:Aldehydes; D034261:Epothilones; D018942:Macrolides; D002857:Chromium; C114026:desoxyepothilone B