Structures and stereochemical assignments of some novel chiral synthons derived from the biotransformation of 2, 3-dihydrobenzofuran and benzofuran by …
…, ND Sharma, R Boyle, JF Malone, J Chima…
Index: Boyd, Derek R.; Sharma, Narain D.; Boyle, Rosemary; Malone, John F.; Chima, Jagdeep; Dalton, Howard Tetrahedron: Asymmetry, 1993 , vol. 4, # 6 p. 1307 - 1324
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Citation Number: 41
Abstract
Abstract Metabolism of 2, 3-dihydrobenzofuran using intact cells of Pseudomonas putida UV4 gave mainly (3S)-3-hydroxy-2, 3-dihydrobenzofuran which was in turn 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- ...
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