Journal
TETRAHEDRON LETTERS
Volume 45, Issue 29, Pages 5577-5579Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2004.05.149
Keywords
macrocyclic dilactone; verbalactone; Barbier-Grignard reaction; sharpless asymmetric dihydroxylation; tosylation; HMG-CoA reductase; kinetic resolution; lactonization
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Verbalactone, a new macrocyclic dilactone was synthesized efficiently in a steroselective manner involving a Barbier-Grignard reaction, a Sharpless asymmetric dihydroxylation, monotosylation, epoxidation, ring opening of the epoxide, hydrolysis and lactonization. A delta-lactone, (+)-(3R,5R)-3-hydroxy-5-decanolide was also formed along with the dimeric lactone. (C) 2004 Elsevier Ltd. All rights reserved.
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