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Enantioselective synthesis of the K-region trans-9,10-dihydrodiol of benzo[g]chrysene

1995; Elsevier BV; Volume: 36; Issue: 34 Linguagem: Inglês

10.1016/0040-4039(95)01243-b

1873-3581

Xiaoqing Tang, Ronald G. Harvey,

Chemical synthesis and alkaloids

Efficient enantioselective syntheses of both enantiomers of the title compound are achieved (>99% ee) via asymmetric dihydroxylation of a stilbene-type precursor using Sharpless catalysts followed by intramolecular biaryl coupling with Pd(PPh3)2Cl2. This is the first example of direct enantioselective synthesis of a K-region dihydrodiol.