Stereocontrolled total synthesis of (-)-callipeltoside A.
[structure: see text] A highly stereocontrolled total synthesis of the cytotoxic macrolide (-)-callipeltoside A has been achieved in 23 steps (4.8% overall). Notable features include a novel asymmetric vinylogous aldol reaction to install the C13 stereocenter and (E)-trisubstituted alkene, an anti-selective aldol addition, a Sonogashira coupling, and, last, a Schmidt-type glycosylation to attach the sugar unit.
University Chemical Laboratory, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK. ip100@cam.ac.uk
Ian
I
Paterson
Robert D M
RD
Davies
Annekatrin C
AC
Heimann
Rodolfo
R
Marquez
Arndt
A
Meyer
D018942:Macrolides / Q000138:chemical synthesis*; D013237:Stereoisomerism
D018942:Macrolides; C410329:callipeltoside A