New Stereoselective Route to the Epoxyquinol Core of Manumycin-Type Natural Products. Synthesis of Enantiopure (+)-Bromoxone,(-)-LL-C10037α, and (+)-KT 8110

…, G Klein, HJ Altenbach, DJ Brauer

Index: Block, Oliver; Klein, Georg; Altenbach, Hans-Josef; Brauer, David J. Journal of Organic Chemistry, 2000 , vol. 65, # 3 p. 716 - 721

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Citation Number: 58

Abstract

A practical route is decribed for the preparation of the C7N core of manumycin-type compounds. Starting from p-benzoquinone, optically pure compounds in both forms can be prepared via enzymatic resolution of a derived diacetoxy conduritol. A diepoxy aminoinositol is accessible which can function for formation of enantiopure epoxyquinones and quinols. Examples are given for acylation reactions of this amine with several acyl derivatives. With ...