M. Koreeda et al., STEREOCONTROLLED SYNTHESIS OF SYN-DIOL AND ANTI-DIOL EPOXIDE METABOLITES OF TRIPHENYLENE, Tetrahedron letters, 37(46), 1996, pp. 8267-8270
The synthesis of both syn- and anti-diol epoxide metabolites of triphe
nylene has been achieved under complete stereochemical control commenc
ing with commercially available 9-phenanthrol in 18% (9 steps) and 37%
(8 steps) overall yields, respectively. The exceptionally high stereo
selectivity of the dimethyldioxirane oxidation of trans-dihydrodiol ha
ving the quasi-diaxially disposed hydroxyl groups is particularly note
worthy. Copyright (C) 1996 Elsevier Science Ltd