New aminocyclitols with quaternary stereocentres via acylnitroso cycloaddition with an ipso,ortho-arene dihydrodiol

Julia Griffen, J White, Gabriele Kociok-Kohn, Matthew Lloyd, Andrew Wells, Tom Arnot, Simon Lewis

Research output: Contribution to journalArticle

31 Citations (Scopus)
144 Downloads (Pure)

Abstract

Microbial ipso,ortho-dihydroxylation of benzoic acid by the B9 mutant strain of Ralstonia eutropha permits rapid construction of aminocyclitols containing a quaternary stereocentre. Installation of the amine functionality is achieved by use of an acylnitroso dienophile for a hetero-Diels–Alder reaction. Both aminotetrols and aminohexols are accessible as single enantiomers by this route. Both NOESY spectroscopic and x-ray crystallographic analyses were required to distinguish cycloadduct isomers. Notably, subsequent to the biooxidation step, all new stereocentres are installed under substrate control. Thus, all stereochemical information is ultimately of enzymatic origin.
Original languageEnglish
Pages (from-to)5989-5997
JournalTetrahedron
Volume69
Issue number29
Early online date18 Apr 2013
DOIs
Publication statusPublished - 22 Jul 2013

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Bioengineering

Fingerprint Dive into the research topics of 'New aminocyclitols with quaternary stereocentres via acylnitroso cycloaddition with an<em> ipso,ortho</em>-arene dihydrodiol'. Together they form a unique fingerprint.

  • Cite this