Enzymatic and chemoenzymatic synthesis of arene trans-dihydrodiols
Data(s) |
02/12/2002
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Resumo |
Several potential approaches to the enzyme-catalysed synthesis of arene trans-diols have been examined including epoxidation/hydrolysis, bis-benzylic hydroxylation, cis-dihydroxylation/alcohol dehydrogenation/ketone reduction, cisdihydroxylation/cis-trans isomerisation. and multi-enzyme synthesis of trans-dihydrodiol secondary metabolites from primary metabolites. The lack of general applicability of these enzymatic methods has led to the development of several chemoenzymatic routes for the synthesis of a series of trans-dihydrodiols from the readily available cis-dihydrodiol precursors. Partial hydrogenation of cis-dihydrodiol metabolites to yield the corresponding cis-tetrahydrodiols followed by a regioselective Mitsunobu inversion process gave trans-tetrahydrodiols that were in turn converted to trans-dihydrodiols. The formation of anti-benzene dioxides or iron tricarbonyl complexes from the corresponding cis-dihydrodiol precursors provided shorter and more convenient chemoenzymatic routes to trans-dihydrodiols. The application of cis-dihydrodiol metabolites of polycyclic azaarenes in the synthesis of the corresponding arene oxides followed by chemical hydrolysis provides a convenient route to trans-dihydrodiols. (C) 2002 Elsevier Science B.V. All rights reserved. |
Identificador |
http://www.scopus.com/inward/record.url?scp=0037010674&partnerID=8YFLogxK |
Idioma(s) |
eng |
Direitos |
info:eu-repo/semantics/restrictedAccess |
Fonte |
Boyd , D & Sharma , N 2002 , ' Enzymatic and chemoenzymatic synthesis of arene trans-dihydrodiols ' JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC , vol 19 , pp. 31-42 . |
Palavras-Chave | #/dk/atira/pure/subjectarea/asjc/1300/1303 #Biochemistry #/dk/atira/pure/subjectarea/asjc/1500/1503 #Catalysis #/dk/atira/pure/subjectarea/asjc/1500/1508 #Process Chemistry and Technology |
Tipo |
article |