Akhtar, MN; Boyd, DR; Hamilton, JG
HEEP COPYRIGHT: BIOL ABS. (-)-Menthyloxyacetyl derivatives of trans-2-bromo-1-hydroxy-1,2,3,4-tetrahydronaphthalene and trans-2-bromo-1-hydroxy-1,2,3,4-tetrahydroanthracene were synthesized and resolved into diastereoisomers by a combination of short-column chromatography and recrystallization. The chiral oxirans naphthalene 1,2-oxide, anthracene 1,2-oxide, 1,2-epoxy-1,2,3,4-tetrahydronaphthalene and 1,2-epoxy-1,2,3,4-tetrahydroanthracene were obtained in a high state of optical purity. The absolute stereochemistry and optical purity of these epoxides were determined by several methods including NMR analysis and correlation with alcohols of known configuration. (The importance of arene oxides in carcinogenesis is discussed.)
