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Published on: June 13, 2022
First total synthesis of (-)-achilleol B: reassignment of its relative stereochemistry
Jesús F Arteaga1, Victoriano Domingo, José F Quílez del Moral
1Department of Organic Chemistry, Institute of Biotechnology, University of Granada, Granada, Spain.
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.
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