Literature DB >> 18496722

Microbial hydroxylation of o-bromophenylacetic acid: synthesis of 4-substituted-2,3-dihydrobenzofurans.

Prashant P Deshpande1, Venkata B Nanduri, Annie Pullockaran, Hamish Christie, Richard H Mueller, Ramesh N Patel.   

Abstract

Microbial hydroxylation of o-bromophenylacetic acid provided 2-bromo-5-hydroxyphenylacetic acid. This enabled a route to the key intermediate 4-bromo-2,3-dihydrobenzofuran for synthesizing a melatonin receptor agonist and sodium hydrogen exchange compounds. Pd-mediated coupling reactions of 4-bromo-2,3-dihydrobenzofuran provided easy access to the 4-substituted-2,3-dihydrobenzofurans.

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Year:  2008        PMID： 18496722     DOI： 10.1007/s10295-008-0363-4

Source DB:  PubMed          Journal:  J Ind Microbiol Biotechnol        ISSN： 1367-5435            Impact factor:   3.346


  12 in total

Review 1.  Enzymatic hydroxylation reactions.

Authors:  H L Holland; H K Weber
Journal:  Curr Opin Biotechnol       Date:  2000-12       Impact factor: 9.740

2.  Heck Reactions in the Presence of P(t-Bu)(3): Expanded Scope and Milder Reaction Conditions for the Coupling of Aryl Chlorides.

Authors:  Adam F. Littke; Gregory C. Fu
Journal:  J Org Chem       Date:  1999-01-08       Impact factor: 4.354

3.  Annulation of aromatic imines via directed C-H activation with Wilkinson's catalyst.

Authors:  R K Thalji; K A Ahrendt; R G Bergman; J A Ellman
Journal:  J Am Chem Soc       Date:  2001-10-03       Impact factor: 15.419

4.  The development of efficient protocols for the palladium-catalyzed cyclization reactions of secondary amides and carbamates.

Authors:  B H Yang; S L Buchwald
Journal:  Org Lett       Date:  1999-07-15       Impact factor: 6.005

5.  Dihydrobenzofuran analogues of hallucinogens. 4. Mescaline derivatives.

Authors:  A P Monte; S R Waldman; D Marona-Lewicka; D B Wainscott; D L Nelson; E Sanders-Bush; D E Nichols
Journal:  J Med Chem       Date:  1997-09-12       Impact factor: 7.446

6.  Synthesis of a tricyclic mescaline analogue by catalytic C-H bond activation.

Authors:  Kateri A Ahrendt; Robert G Bergman; Jonathan A Ellman
Journal:  Org Lett       Date:  2003-04-17       Impact factor: 6.005

7.  Enantioselective alpha-hydroxylation of 2-arylacetic acid derivatives and buspirone catalyzed by engineered cytochrome P450 BM-3.

Authors:  Marco Landwehr; Lisa Hochrein; Christopher R Otey; Alex Kasrayan; Jan-E Bäckvall; Frances H Arnold
Journal:  J Am Chem Soc       Date:  2006-05-10       Impact factor: 15.419

8.  Novel phacB-encoded cytochrome P450 monooxygenase from Aspergillus nidulans with 3-hydroxyphenylacetate 6-hydroxylase and 3,4-dihydroxyphenylacetate 6-hydroxylase activities.

Authors:  Francisco Ferrer-Sevillano; José M Fernández-Cañón
Journal:  Eukaryot Cell       Date:  2006-12-22

9.  Arylcyclopropanecarboxyl guanidines as novel, potent, and selective inhibitors of the sodium hydrogen exchanger isoform-1.

Authors:  S Ahmad; L M Doweyko; S Dugar; N Grazier; K Ngu; S C Wu; K J Yost; B C Chen; J Z Gougoutas; J D DiMarco; S J Lan; B J Gavin; A Y Chen; C R Dorso; R Serafino; M Kirby; K S Atwal
Journal:  J Med Chem       Date:  2001-09-27       Impact factor: 7.446

10.  Catabolism of aromatic acids in Trichosporon cutaneum.

Authors:  J J Anderson; S Dagley
Journal:  J Bacteriol       Date:  1980-02       Impact factor: 3.490
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  2 in total

1.  2-(2-Bromo-phen-yl)acetic acid.

Authors:  Rajni Kant; Kamini Kapoor; B Narayana
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-05-12

2.  2-(2-Chloro-phen-yl)acetic acid.

Authors:  Rajni Kant; Vivek K Gupta; Kamini Kapoor; B Narayana
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-05-31
  2 in total

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