Stereocontrolled total synthesis of (-)-callipeltoside A.

Autor: Paterson I; University Chemical Laboratory, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK. ip100@cam.ac.uk, Davies RD, Heimann AC, Marquez R, Meyer A
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2003 Nov 13; Vol. 5 (23), pp. 4477-80.
DOI: 10.1021/ol0357853
Abstrakt: [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.
Databáze: MEDLINE