Abstract
A second-generation approach to the BC spirocycle of ‘upenamide is reported. Central to the synthesis is an endo selective Diels–Alder reaction between 1-(t-butyldimethylsiloxy)-1,3-butadiene and bromomaleic anhydride followed by a radical mediated allylation of the ring fusion bromide. Functional group manipulation provides three (9–11) advanced synthetic intermediates ready for coupling with the remaining half (DE bicycle) of ‘upenamide.
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