Enantioselective preparation of the C1-C11 fragment of apoptolidin.
[reaction: see text] A novel approach toward the synthesis of the triene portion of the biologically active polyketide apoptolidin is described. The use of an iterative thionyl chloride rearrangement/oxidation sequence to construct trisubstituted olefins is explored.
Paquette
William D
WD
Department of Chemistry & Biochemistry and the Walther Cancer Research Center, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, Indiana 46556-5670, USA.
Taylor
Richard E
RE
D000475:Alkenes / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis*; D008956:Models, Chemical; D015394:Molecular Structure; D013237:Stereoisomerism
D000475:Alkenes; D018942:Macrolides; C114125:apoptolidin