Stereoselective Synthesis of (10S,12S)-10-Hydroxy-12-methyl-1-oxacyclo­dodecane-2,5-dione via Prins Cyclization

 

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Abstract

The total synthesis of (10S,12S)-10-hydroxy-12-methyl-1-oxacyclododecane-2,5-dione is described proving the versatility of the Prins cyclization in natural products synthesis. The approach is convergent and highly stereoselective. Prins cyclization, esterification, ring-closing metathesis and oxidation reactions are utilized as key steps in the synthesis of this macrolactone.

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