Efficient stereochemical relay en route to leucascandrolide A.
[structure: see text]. A complete relay of the initial stereochemical information is central to the efficient and highly stereocontrolled construction of the C1-C15 fragment of the marine macrolide leucascandrolide A. Cyclic silane 3, assembled via Pt-catalyzed hydrosilylation, was designed to serve as a temporary template for the installation of the C12 stereogenic center. The strategy features a highly convergent C10-C11 bond construction via 1,5-anti-selective aldol reaction and rapid assembly of the trisubstituted pyran subunit via Prins desymmetrization.
Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA. skozmin@uchicago.edu
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D000818:Animals; D007202:Indicators and Reagents; D011161:Porifera / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D013237:Stereoisomerism
D007202:Indicators and Reagents; D012717:Sesquiterpenes; C408748:leucascandrolide A