Asymmetric synthesis of the chlorocyclopropane-containing callipeltoside A side chain.
[reaction: see text] The callipeltoside A chlorocyclopropyl-containing dienyne side chain has been synthesized in nine steps and 33% overall yield from commercially available 1,2,5,6-O-dicyclohexylidene-D-mannitol. The key steps in the synthesis are a highly diastereoselective cyclopropanation of a vinyl chloride allylic ether and a Suzuki cross-coupling to complete the carbon framework.
Evans
D A
DA
Department of Chemistry & Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA. evans@chemistry.harvard.edu
Burch
J D
JD
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D003521:Cyclopropanes / Q000138:chemical synthesis*; D018942:Macrolides; D008353:Mannitol / Q000031:analogs & derivatives / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
C424062:1,2,5,6-O-dicyclohexylidenemannitol; D000900:Anti-Bacterial Agents; D003521:Cyclopropanes; D018942:Macrolides; C410329:callipeltoside A; D008353:Mannitol