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J Am Chem Soc. 2002 Mar 13;124(10):2080-1.

The total synthesis of (+/-)-merrilactone A.

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  • 1Department of Chemistry, Columbia University, Havemeyer Hall, New York, New York 10027, USA.

Abstract

The total synthesis of the title compound has been accomplished in 20 steps. The key step is a free radical cyclization of vinyl bromide 29 to afford 30. The synthesis also features an efficient Dielsminus signAlder reaction of 2,3-dimethylmaleic anhydride with 1-(tert-butyldimethylsiloxy)-butadiene. The oxetane moiety of merrilactone A is fashioned via a Payne-like rearrangement of a hydroxyepoxide (see 2 right arrow 1).

PMID:
11878938
[PubMed - indexed for MEDLINE]
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