Synthetic studies on neomarinone: practical and efficient stereoselective synthesis of the side chain.

Suárez, R. M.; Martínez, M. M.; Sarandeses, L. A.; Pérez Sestelo, J.

Abstract

Tetrahedron Lett. 2007, 48, 6493–6495 (DOI: 10.1016/j.tetlet.2007.07.064).

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A practical and efficient stereoselective synthesis of the side chain of neomarinone is reported. The synthesis was achieved in six steps (41% overall yield) from 2-methyl-2-cyclohexenone. The key step is a novel stereoselective 1,4-conjugate addition/enolate alkylation by an epoxide-opening reaction.