Resolution of polycyclic aromatic hydrocarbon dihydrodiols via diastereomeric formaldehyde acetals

Tetrahedron Asymmetry

Volumn 8, Issue 20, 1997, Pages 3375-3378

  Lakshman, Mahesh K ^a   Chaturvedi, Surendrakumar ^a   Kole, Panna L ^a   Windels, James H ^a   Myers, Mark B ^a   Brown, Michael A ^a  

^a Chemsyn Science Laboratories   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARCINOGEN; DIHYDRODIOL DEHYDROGENASE; FORMALDEHYDE; POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; DIASTEREOISOMER; OPTICAL RESOLUTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIC MIXTURE; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0030721531     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00464-3     Document Type: Article

References (15)

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11. McCaustland, D. J.; Engel, J. F. Tetrahedron Lett. 1975, 2549-2552. Lehr, R. E.; Schaefer-Ridder, M.; Jerina, D. M. J. Org. Chem. 1977, 42, 736-744. Harvey, R. G. In Polycyclic Hydrocarbons and Carcinogenesis; Harvey, R. G. Ed.; ACS Symposium Series 283, American Chemical Society: Washington, DC, 1985; pp 35-62.
12. McCaustland, D. J.; Engel, J. F. Tetrahedron Lett. 1975, 2549-2552. Lehr, R. E.; Schaefer-Ridder, M.; Jerina, D. M. J. Org. Chem. 1977, 42, 736-744. Harvey, R. G. In Polycyclic Hydrocarbons and Carcinogenesis; Harvey, R. G. Ed.; ACS Symposium Series 283, American Chemical Society: Washington, DC, 1985; pp 35-62.
13. 4 and evaporated. Chromatography of the crude product over silica gel using 2% EtOAc in hexane afforded the diastereomeric mixture 2 as a light yellow foam. This material was directly subjected to HPLC in 10-12 mg aliquots.
14. D=-71.1 (c=4.5 mg/mL, THF).
15. 2O-acetone or by chromatography (silica gel, 1:1 THF-hexane) afforded the dihydrodiol (84 mg, 0.29 mmol) in 64% yield.