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 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.
Arteaga
Jesús F
JF
Department of Organic Chemistry, Institute of Biotechnology, University of Granada, Granada, Spain.
Domingo
Victoriano
V
Quílez del Moral
José F
JF
Barrero
Alejandro F
AF
D031162:Achillea / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry*; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry*
D013729:Terpenes; D014315:Triterpenes; C530507:achilleol B; C009884:geranylacetone