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Synthesis 2010(1): 73-78
DOI: 10.1055/s-0029-1217107
DOI: 10.1055/s-0029-1217107
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Stereoselective Synthesis of (10S,12S)-10-Hydroxy-12-methyl-1-oxacyclododecane-2,5-dione via Prins Cyclization
Further Information
Received
29 July 2009
Publication Date:
24 November 2009 (online)
Publication History
Publication Date:
24 November 2009 (online)
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.
Key words
Prins cyclization - esterification - ring-closing metathesis - macrolactone
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