Tetrahedron p. 4467 - 4480 (1999)
Update date:2022-08-11
Topics:
Cavallotti, Camilla
Orsini, Fulvia
Sello, Guido
Di Gennaro, Patrizia
Galli, Enrica
Bestetti, Giuseppina
1,2-Dihydroxynaphthalenes are produced by dehydrogenation of the corresponding 1,2-dihydro-1,2-dihydroxynaphthalenes using an Escherichia coli recombinant strain containing the dihydrodiol naphthalene dehydrogenase gene cloned from Pseudomonas fluorescens N3. Conversions are led in carefully controlled conditions to minimise product polymerisation. A multistep procedure using a weakly basic resin permits isolation of good product amounts, solving the toxicity problem. Products are isolated and characterised as t-butyldimethylsilyl derivatives that are stable compounds. The transformation of the 1,2-dihydroxynaphthalenes into the corresponding 1,2-naphthoquinones is also reported.
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