Efficient Stereochemical Relay en Route to Leucascandrolide A
journal contributionposted on 16.02.2001, 00:00 by Sergey A. Kozmin
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.
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strategy featuresconvergentCyclic silane 3Leucascandrolidestereocontrolled constructionhydrosilylationtemplateC 12 stereogenic centerassemblyfragmentPrins desymmetrizationaldol reactiontrisubstituted pyran subunitinstallationmarine macrolide leucascandrolidestereochemical informationEfficient Stereochemical Relaybond