A highly enantio selective synthesis of (-)- and (+)-juglomycin A through Dotz annulation and asymmetric dihydroxylation

A highly enantioselective synthesis of (-)- and (+)-juglomycin A, a quinone antibiotic is described. The synthesis is completed in eight steps, and 19% overall yield and in a high enantioselectivity of 99.5% [for (-)-juglomycin A] and 98.5% [for (+)-juglomycin A]. The synthetic strategy features an efficient combination of the Dotz annulation reaction and asymmetric dihydroxylation as the keys steps. (c) 2008 Elsevier Ltd. All rights reserved.