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Chemical and enzyme-catalysed syntheses of enantiopure epoxide and diol derivatives of chromene, 2,2-dimethylchromene, and 7-methoxy-2,2-dimethylchromene (precocene-1)

DOI: 10.1039/p19960001757

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1757 - 1765 (1996)

Update date:2022-07-29

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Authors:

Boyd, Derek R.Boyd, Derek R.

Sharma, Narain D.Sharma, Narain D.

Boyle, RosemaryBoyle, Rosemary

Evans, Timothy A.Evans, Timothy A.

Malone, John F.Malone, John F.

McCombe, Kenneth M.McCombe, Kenneth M.

Dalton, HowardDalton, Howard

Chima, JagdeepChima, Jagdeep

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Article abstract of DOI:10.1039/p19960001757

Procaryotic (bacterial) dioxygenase-catalysed asymmetric dihydroxylation of chromene and 2,2-dimethylchromene to yield the (4S)-enantiomers of the corresponding cis-diols exclusively is reported. The epoxide, and derived cis- and trans-diol products from the previously reported eucaryotic (mammalian) metabolism of precocene-1 (7-methoxy-2,2-dimethylchromene), and the corresponding epoxide and diol derivatives of chromene and 2,2-dimethylchromene, have now been obtained in enantiopure form by chemical resolution of the corresponding bromohydrins using methoxy-(trifluoromethyl)phenylacetic acid (MTPA) or camphanate esters. The absolute configurations of the epoxides, cis- and trans-diols have been determined by chemical synthesis from, and stereochemical correlation with, the corresponding camphanate and MTPA esters. X-Ray crystal structure analysis has provided an unequivocal method for assignment of the absolute stereochemistry in each case.

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Product name:(+)-(3R,4S)-cis-Chromane-3,4-diol

Cas No:146503-06-2

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