The Total Synthesis of (±)-Merrilactone A
- 16 February 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (10), 2080-2081
- https://doi.org/10.1021/ja012495d
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 Diels−Alder 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 → 1).Keywords
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