Pure Appl. Chem., 2007, Vol. 79, No. 4, pp. 667-676
http://dx.doi.org/10.1351/pac200779040667
Progress toward a total synthesis of spirastrellolide A
Abstract:
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.
Keywords
aldol; anticancer; macrolides; natural products; spiroacetal; stereocontrolled synthesis.