Cascade assembly of the benzo[a]anthraquinone ring system common to the angucycline antibiotics.

ABSTRACT: A benzo[a]anthraquinone ring system, common to a group of angucycline antibiotics, has been prepared by a unique cascade of reactions. The reaction sequence was initiated by a Suzuki-Miyaura cross-coupling between a bromoquinone and vinyl boronic anhdyride. The reaction product is proposed to undergo a 6π-electron cyclization triggered by reductive activation of the quinone. The reaction process is proposed to be autocatalytic.

SUBMITTER: Baranczak A 

PROVIDER: S-EPMC3287049 | biostudies-literature | 2012 Mar

REPOSITORIES: biostudies-literature