ChemInform Abstract: Asymmetric Synthesis of Alkannin and Shikonin.
Abstract
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ChemInform Abstract
A new route for the synthesis of the fully protected shikonin (VII) is described. The procedure is based on the condensation of an 1,4-dipole equivalent with the Michael acceptor acrylonitrile (II) to construct the polyoxygenated aromatic ring system and the introduction of the chiral center via an asymmetric allyl boration. Using the antipode of the allyl boration reagent leads to the synthesis of (-)-alkannin.
