Stereocontrolled total synthesis of (-)-callipeltoside A |
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Authors: | Paterson Ian Davies Robert D M Heimann Annekatrin C Marquez Rodolfo Meyer Arndt |
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Affiliation: | University Chemical Laboratory, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK. ip100@cam.ac.uk |
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Abstract: | [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. |
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