Studies in macrolide synthesis: A stereocontrolled synthesis of oleandolide employing reagent- and substrate-controlled aldol reactions of (S)-1-(benzyloxy)-2-methylpentan-3-one

Article abstract of DOI:10.1021/ja00104a010

A highly stereocontrolled total synthesis of oleandolide (2), the aglycon of the macrolide antibiotic oleandomycin (1), has been completed in 8% overall yield (20 steps longest linear sequence, 26 steps in total) with 90% overall diastereoselectivity. Ini