Stereocontrolled synthesis of syn- and anti-diol epoxide metabolites of triphenylene
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.
Koreeda, Masato,Gopalaswamy, Ramesh,Yang, Jinhai,Tuinman, Roeland J.
p. 8267 - 8270
(2007/10/03)
Synthesis of Triphenylene 1,2-Oxide (1,2-Epoxy-1,2-dihydrophenylene) and Absolute Configuration of the trans-1,2-Dihydro Diol Metabolite of Triphenylene. Crystal Structure of (-)-(1R,2R)-trans-2-Bromo-1-menthyloxyacetoxy-1,2,3,4-tetrahydrotriphenylene
The synthesis of triphenylene 1,2-oxide (1,2-epoxy-1,2-dihydrotriphenylene) (2) from both racemic and optically pure precursors is reported.Racemic triphenylene 1,2-oxide (2) was obtained in each case, in accord with PMO calculations which predict rapid r
Boyd, Derek R.,Kennedy, Deirdre A.,Malone, John F.,O'Kaine, Gerard A.
p. 369 - 376
(2007/10/02)
Efficient Synthesis of Non-K-Region trans-Dihydro Diols of Polycyclic Aromatic Hydrocarbons from o-Quinones and Catechols
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Platt, Karl L.,Oesch, Franz
p. 265 - 268
(2007/10/02)
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