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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)
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UNSPECIFIED (1996) Chemical and enzyme-catalysed syntheses of enantiopure epoxide and diol derivatives of chromene, 2,2-dimethylchromene, and 7-methoxy-2,2-dimethylchromene (precocene-1). JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 (14). pp. 1757-1765. ISSN 0300-922X
Full text not available from this repository.Abstract
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.
| Item Type: | Journal Article |
|---|---|
| Subjects: | Q Science > QD Chemistry |
| Journal or Publication Title: | JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 |
| Publisher: | ROYAL SOC CHEMISTRY |
| ISSN: | 0300-922X |
| Date: | 21 July 1996 |
| Number: | 14 |
| Number of Pages: | 9 |
| Page Range: | pp. 1757-1765 |
| Publication Status: | Published |
| URI: | http://wrap.warwick.ac.uk/id/eprint/18547 |
Data sourced from Thomson Reuters' Web of Knowledge
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