STEREOCONTROLLED SYNTHESIS OF SYN-DIOL AND ANTI-DIOL EPOXIDE METABOLITES OF TRIPHENYLENE

Authors
KOREEDA M GOPALASWAMY R YANG JH TUINMAN RJ
Citation
M. Koreeda et al., STEREOCONTROLLED SYNTHESIS OF SYN-DIOL AND ANTI-DIOL EPOXIDE METABOLITES OF TRIPHENYLENE, Tetrahedron letters, 37(46), 1996, pp. 8267-8270
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
46
Year of publication
1996
Pages
8267 - 8270
Database
ISI
SICI code
0040-4039(1996)37:46<8267:SSOSAA>2.0.ZU;2-W
Abstract
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