Journal
PURE AND APPLIED CHEMISTRY
Volume 79, Issue 4, Pages 667-676Publisher
WALTER DE GRUYTER GMBH
DOI: 10.1351/pac200779040667
Keywords
natural products; macrolides; anticancer; stereocontrolled synthesis; spiroacetal; aldol
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Funding
- Engineering and Physical Sciences Research Council [EP/C541677/1] Funding Source: researchfish
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Progress toward a total synthesis of spirastrellolide A, a 38-membered marine macrolide, is reported. Syntheses of two diastereomers of the C1-C25 region, and an evolving Sharpless dihydroxylation strategy toward a C26-C40 fragment, are described. The syntheses exploit boron-mediated aldol chemistry to install key stereocenters, and feature late-stage thermodynamically controlled spiroacetalizations.
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