ChemInform Abstract: Total Synthesis of Granditropone, Grandirubrine, Imerubrine, and Isoimerubrine.
Abstract
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ChemInform Abstract
(4 + 2) Cycloaddition reaction of the α-pyron (I) with the cyclopropenone ketal (II) followed by acid treatment predominantly provides granditropone (III) the key intermediate tropone for the naturally occurring title tropoloisoquinolines. Regioselective hydroxylation of (III) gives grandirubrine (IV) and O-methylation yields both imerubrine (VI) and isoimerubrine (VII), which can be separated by SiO2 chromatography.
