Abstract
The formal total synthesis of the myxobacteria metabolite (−)-apicularen A ( 1) is described. The key step utilized to construct the 2,6- trans-disubstituted tetrahydropyran ring was the transannular oxy-Michael addition of enone (+)- 48 to form trans-pyranone (+)- 50. Cyclisation of the C13 epimer (−)- 49 also gave the same trans-pyranone (+)- 50 demonstrating that the stereochemistry of the apicualren ring system can be controlled only by the C15 asymmetric centre. Reduction of the ketone in (+)- 50 and demethylation gave the advanced apicularen intermediate 4 completing the formal total synthesis of the natural product 1.
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