Self-consistent synthesis of the squalene synthase inhibitor zaragozic acid C via controlled oligomerization.

ABSTRACT: Despite the prevalence of repeating subunits in chiral natural products, stereocontrolled oligomerization is a largely unexplored strategy for construction of carbon skeletal frameworks. This report describes the use of silyl glyoxylates as dipolar glycolic acid synthons in a controlled oligomerization reaction for the efficient construction of the squalene synthase inhibitor zaragozic acid C. This new methodology allows rapid, stereocontrolled formation of the carbon skeleton with a desirable protecting group scheme while minimizing functional group repair and oxidation state manipulations.

SUBMITTER: Nicewicz DA 

PROVIDER: S-EPMC2643040 | biostudies-literature | 2008 Dec

REPOSITORIES: biostudies-literature