Download PDF
Synlett 1992; 1992(5): 391-393
DOI: 10.1055/s-1992-21355
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Microbial Oxidation of o-Chlorostyrene: Determination of Absolute Stereochemistry of the cis-Diol Metabolite by a Convergent Synthesis Utilizing an Intramolecular Diels-Alder Reaction

Tomas Hudlicky* , Eric E. Boros, Christie H. Boros
  • *Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg, Virginia 24061-0212, USA
Further Information

Publication History

Publication Date:
08 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

The structures of the diol metabolites 2a and 3a of o-chlorostyrene (1a) from the bacterium Pseudomonas putida strain 39D were established. Absolute stereochemistry of the cis-diol 2a was determined by a convergent synthesis of an oxatricyclodecane derivative 8 [3a-ethyl-7-dimethylthexylperhydro-3,6-methanobenzofuran] utilizing the known cis-diol metabolite 2b of styrene and an intramolecular Diels-Alder reaction.

      >