Enantioselective synthesis of the tumorigenic anti-diol epoxide metabolites of benzo[a]pyrene
1995; Elsevier BV; Volume: 36; Issue: 16 Linguagem: Inglês
10.1016/0040-4039(95)00385-p
ISSN1873-3581
AutoresRonald G. Harvey, Xiaoqing Tang,
Tópico(s)Asymmetric Synthesis and Catalysis
ResumoEfficient, highly enantioselective syntheses of (+) and (−)-anti-benzo[a]pyrene diol epoxide (BPDE) from 9,10-dihydrobenzo[a]pyrene are described. Initial epoxidation catalyzed by (salen) Mn(III) complex gives 7,8-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (>90% ee). Acid-catalyzed hydration occurs regio- and stereo-selectively to furnish the trans-tetrahydrodiols which are converted into the optically active anti-BPDEs.
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