Journal of the Chemical Society. Perkin transactions I p. 2233 - 2238 (1981)
Update date:2022-08-06
Topics:
Boyd, Derek R.
Gadaginamath, Guru S.
Sharma, Narain D.
Drake, Alexander F.
Mason, Stephen F.
Jerina, Donald M.
(+)-Benzanthracene 10,11-oxide (9) has been obtained in optically pure form by a four-step synthesis from (-)-trans-(10R,11R)-10-bromo-11-(menthyloxyacetoxy)-8,9,10,11-tetrahydrobenzanthracene (1A) which was separated from diastereoisomer (1B) by recrystallisation.The absolute configuration of (+)-(9) was established as (10S, 11R) by application of the excition-chirality method to the circular dichroism curve of the benzoate (+)-(6) and by a correlation of stereochemistry between (+)-(6), (-)-(4), and (+)-(9). (+)-Benzanthracene 5,6-oxide (15) has been synthesised in 30percent optical yield using partially resolved (+)-cis-5,6-dihydroxy-5,6-dihydrobenzanthracene (11) obtainable by chromatographic resolution of the (-)-cis-5,6-dimethyloxyacetoxy-5,6-dihydrobenzanthracene diastereoisomers (12A) and (12B).Both arene oxides, (+)-(9) and (+)-(15), showed configurational stability at ambient temperature in accord with perturbation molecular orbital calculations.
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Doi:10.1055/s-1981-29539
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(1981)Doi:10.1016/j.tet.2004.08.026
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