From Central to Axial to Central Chirality: Enantioselective Construction of the trans??4, 5, 9, 10??Tetrahydroxy??9, 10??dihydrophenanthrene System

G Stavrakov, M Keller, B Breit

Index: Stavrakov, Georgi; Keller, Manfred; Breit, Bernhard European Journal of Organic Chemistry, 2007 , # 34 p. 5726 - 5733

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Citation Number: 15

Abstract

Abstract Enantioselective synthesis of the core trans-4, 5, 9, 10-tetrahydroxy-9, 10- dihydrophenanthrene parent system of the antibiotics benanimicin, pradimicin and FD 594 has been accomplished. The synthesis employs a chiral tether approach and makes use of efficient central to axial to central chirality transfer. Key to success was an “imine-directed” atropdiastereoselective Ullmann coupling under mild reaction conditions.(© Wiley-VCH ...