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Synthesis of (+)- and (−)-benzo[a]pyrene 7,8-oxide

✍ Scribed by Derek R. Boyd; Guru S. Gadaginamath; Robert Hamilton; Haruhiko Yagi; Donald M. Jerina

Publisher: Elsevier Science
Year: 1978
Tongue: French
Weight: 227 KB
Volume: 19
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)94807-5

No coin nor oath required. For personal study only.

✦ Synopsis

The concept of stereoselectivity during monooxygenase catalyzed addition of an oxygen atom to the stereoheterotopic faces of a polycyclic aromatic hydrocarbon (PAH) was initially proposed' on the basis of (a) liver microsomal metabolism studies on naphthalene and (+)-naphthalene 1,2-oxide and (b) synthesis of partially resolved naphthalene 1,2-oxide. Synthesis of optically pure naphthalene-and anthracene 1,2-oxide was subsequently achieved by a combination of short-column chromatography and recrystallization of the trans-2-bromo-l-menthyloxyacetoxy-1,2,3,4-tetrahydro diastereomers of naphthalene and anthracene. 2,3 Recent studies of the metabolically formed transdihydrodiols of the potent carcinogen benzo[a]pyrene (B[a]P) have indicated that a high degree of stereoselectivity occurs during their formation. 4 The trans-7,8-dihydrodiol obtained by liver

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