The total synthesis of alternaric acid and progress toward the synthesis of subglutinol

Abstract

The Oshima-Utimoto reaction coupling an allylic alcohol and butyl vinyl ether is utilized to construct the furan ring of the natural product subglutinol B. Methodology for the diastereoselective substitution of furans is also reported. Methodology utilizing silylglyoxylates as latent acyl anions for use in stereoselective multicomponent reactions is developed in the form of addition of carbon nucleophiles followed by an intermolecular aldol reaction. This methodology was then applied towards the total synthesis of alternaric acid

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