Tetrahedron Letters p. 8267 - 8270 (1996)
Update date:2022-08-02
Topics:
Koreeda, Masato
Gopalaswamy, Ramesh
Yang, Jinhai
Tuinman, Roeland J.
The synthesis of both syn- and anti-diol epoxide metabolites of triphenylene has been achieved under complete stereochemical control commencing with commercially available 9-phenanthrol in 18% (9 steps) and 37% (8 steps) overall yields, respectively. The exceptionally high stereoselectivity of the dimethyldioxirane oxidation of trans-dihydrodiol having the quasi-diaxially disposed hydroxyl groups is particularly noteworthy.
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Doi:10.1039/jr9650001495
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