UNSPECIFIED (1993) STRUCTURES AND STEREOCHEMICAL ASSIGNMENTS OF SOME NOVEL CHIRAL SYNTHONS DERIVED FROM THE BIOTRANSFORMATION OF 2,3-DIHYDROBENZOFURAN AND BENZOFURAN BY PSEUDOMONAS-PUTIDA. TETRAHEDRON-ASYMMETRY, 4 (6). pp. 1307-1324. ISSN 0957-4166

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Abstract

Metabolism of 2,3-dihydrobenzofuran using intact cells of Pseudomonas puyida UV4 gave mainly (3S)-3-hydroxy-2,3-dihydrobenzofuran which was in tum oxidized to an unstable intermediate, (3S,4R,5S)-3,4,5-trihydroxy-2,3,4,5-tetrahydrobenzofuran. Spontaneous dehydration of this cis,cis-triol occurred in the carbocyclic ring to give (3S)-3,5-dihydroxy 2,3-dihydrobenzofuran and in the heterocyclic ring to yield (4R,5S)-cis-4,5-dihydroxy-4,5-dihydrobenzofuran. Bacterial metabolism of benzofuran was found to occur in the carbocyclic ring to form (6S,7S)-cis-6,7-dihydroxy-6,7-dihydrobenzofuran and its dehydration product, 6-hydroxybenzofuran. Dioxygenase-catalysed cis-dihydrodiol formation in the heterocyclic ring of benzofuran (to give cis-2,3-dihydroxy-2,3-dihydrobenzofuran as a transient intermediate) is proposed to account for the appearance of (1R)-1,2-dihydroxy-1-(2'-hydroxyphenyl)ethane as a major metabolite of benzofuran. cis-4,5-Dihydroxy-4,5-dihydrobenzofuran and cis-6,7-dihydroxy-6,7-dihydrobenzofuran are potentially valuable chiral synthons which can be added to the small pool of bicyclic cis-dihydrodiol metabolites currently available for synthesis.

Item Type:	Journal Article
Subjects:	Q Science > QD Chemistry
Journal or Publication Title:	TETRAHEDRON-ASYMMETRY
Publisher:	PERGAMON-ELSEVIER SCIENCE LTD
ISSN:	0957-4166
Date:	June 1993
Volume:	4
Number:	6
Number of Pages:	18
Page Range:	pp. 1307-1324
Publication Status:	Published
URI:	http://wrap.warwick.ac.uk/id/eprint/21307

Data sourced from Thomson Reuters' Web of Knowledge

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