First total synthesis of (-)-achilleol B: reassignment of its relative stereochemistry.

Jesús F Arteaga, Victoriano Domingo, José F Quílez del Moral, Alejandro F Barrero

Index: Org. Lett. 10(9) , 1723-6, (2008)

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Abstract

The first total synthesis of (-)-achilleol B was achieved using a convergent approach with a longest linear sequence of 14 steps. Three key steps were employed, including an enantioselective Robinson annelation for the construction of the bicyclic moiety. The monocyclic synthon was prepared through a Ti(III)-mediated cylization of a chiral monoepoxide obtained via asymmetric dihydroxylation of geranylacetone. The asymmetric preparation of these subunits also permitted us to achieve the enantioselective synthesis of elegansidiol, achilleol A, and farnesiferol B.