Stereocontrolled synthesis of syn- and anti-diol epoxide metabolites of triphenylene

Tetrahedron Letters

Volumn 37, Issue 46, 1996, Pages 8267-8270

  Koreeda, Masato ^a   Gopalaswamy, Ramesh ^a   Yang, Jinhai ^a   Tuinman, Roeland J ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG METABOLITE; EPOXIDE; POLYCYCLIC AROMATIC HYDROCARBON; TRIPHENYLENE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030580329     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01896-5     Document Type: Article

References (19)

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10. 3 treatment of the diacetate derivative (i.e., the diacetate derivative instead of the cyclic carbonate in 12) was found to be relatively unstable, presumably due to the favorable trans-diaxial orientation between the vicinal bromoacetate groups.
11. 4: C, 74.99; H, 3.98. Found: C, 74.63; H, 3.78.
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15. 6) δ 4.43 (br dd, 1H, J = 5.6, 1.8 Hz), 5.42 (br s, 1H), 6.48 (ddd, 1H, J = 9.9, 5.6, 1.1 Hz), 7.56 (d, 1H, J = 9.9 Hz), 7.65-7.73 (m, 2H), 8.42-8.47 (m, 2H), 8.83-8.89 (m, 2H).
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19. 14. For the dimethyldioxirane epoxidation of non-bay-region trans-dihydrodiols, see: Kumar, S. Tetrahedron Lett. 1996, 37, 1527-1530.