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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

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

Nicewicz David A DA Satterfield Andrew D AD Schmitt Daniel C DC Johnson Jeffrey S JS

Journal of the American Chemical Society 20081201 51

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 p ...[more]

PMID: 19053214

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