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First Total Synthesis of (−)-Achilleol B: Reassignment of Its Relative Stereochemistry

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...

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Bibliographic Details
Published in:Organic letters 2008-05, Vol.10 (9), p.1723-1726
Main Authors: Arteaga, Jesús F, Domingo, Victoriano, Quílez del Moral, José F, Barrero, Alejandro F
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol800326n