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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.


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).

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