Regio- and stereo-selective dioxygenase-catalysed cis-dihydroxylation of fjord-region polycyclic arenes

Derek Boyd, Narain Sharma, J.S. Harrison, M.A. Kennedy, Christopher Allen, D.T. Gibson

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14 Citations (Scopus)

Abstract

Bacterial dioxygenase-catalysed cis-dihydroxylation of the tetracyclic arenes benzo[c]phenanthrene 2, and the isosteric compounds benzo[b]naphtho[1,2-d]furan 8, and benzo[b]naphtho[1,2-d]thiophene 9, has been found to occur exclusively at fjord-region bonds. The resulting cis-dihydrodiols 7, 10 and 11 were found to be enantiopure and of similar absolute configuration. cis-Dihydroxylation was also observed in the pseudo-fjord region of the 8,9,10,11-tetrahydro-precursors (12 and 13) of benzo[b]naphtho[1,2-d]furan 8, and benzo[b]naphtho[1,2-d]thiophene 9, to yield the corresponding enantiopure hexahydro cis-diols 14 and 15. A novel tandem cis-dihydroxylation and bis-desaturation of the tetrahydro-substrate, tetrahydrobenzo[b]naphtho[1,2-d]thiophene 13, catalysed by biphenyl dioxygenase, was found to yield the fjord-region cis-dihydrodiol 17 of benzo[b]naphtho[1,2-d]thiophene 9.
Original languageEnglish
Pages (from-to)1264-1269
Number of pages6
JournalJournal of the Chemical Society - Perkin Transactions 1
Volume1
Issue number11
DOIs
Publication statusPublished - 2001

ASJC Scopus subject areas

  • Chemistry(all)

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