I. Paterson et al., THE TOTAL SYNTHESIS OF SWINHOLIDE-A .3. A STEREOCONTROLLED SYNTHESIS OF (-)-PRE-SWINHOLIDE-A, Tetrahedron, 51(34), 1995, pp. 9437-9466
Two coupling strategies for (-)-pre-swinholide A were devised based on
the analysis in Scheme 1. In the first route, a boron-mediated aldol
reaction between the ethyl ketone 19 and the aldehyde 3 was used to co
nstruct the C-15-C-16 bond with moderate diastereoselectivity. In the
second route, a Mukaiyama aldol reaction between the methyl ketone 54
and the aldehyde 4 introduced the C-18-C-19 bond with complete stereoc
ontrol.