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Efficient resolution of the dihydrodiol derivatives of benzo[a]pyrene by high-pressure liquid chromatography of the related (−)-dimenthoxyacetates

✍ Scribed by Ronald G. Harvey; Hee Cho

Publisher
Elsevier Science
Year
1977
Tongue
English
Weight
354 KB
Volume
80
Category
Article
ISSN
0003-2697

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✦ Synopsis

The diastereomeric (-)-dimenthoxyacetate derivatives of (t)-tram-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene were efficiently resolved by high-pressure liquid chromatography (HPLC) on silica gel. Treatment with methanolic ammonia under mild conditions removed the menthoxyacetate groups to furnish the optically pure (+) and (-) enantiomers of the trans-dihydrodiol.

Epoxidation of each of the latter with m-chloroperbenzoic acid gave the corresponding (-) and (+) antidiolepoxides. The speed and efficiency of resolution of these relatively sensitive compounds by HPLC demonstrates the potential utility of this technique for resolution of all types of carcinogen-derived arene dihydrodiols.

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