Download PDF
Synlett 1993; 1993(3): 177-185
DOI: 10.1055/s-1993-22393
account
© 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.

Ring Opening Reactions of Oxabicyclic Compounds as a Route to Cyclic and Acyclic Compounds with Multiple Stereocenters

Mark Lautens*
  • *Department of Chemistry, University of Toronto, Toronto, Ontario, Canada M5S 1A1
Further Information

Publication History

Publication Date:
19 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

The ring opening of oxabicyclic compounds with a variety of nucleophiles can serve as a useful reaction for the synthesis of cyclic and acyclic compounds with multiple stereocenters. Highly regio- and stereoselective reactions have been observed with organocuprates, silylcuprates, organolithium reagents and organomagnesium compounds. 1. Introduction 2. Research Plan and Related Literature Information 3. Organocuprate Openings 4. Organolithium Openings of Oxabicyclo[3.2.1] Systems 5. Oxidative Cleavage of the Ring 6. Rifamycin S Subunit and the endo Alkoxy Effect 7. Regioselective Ring Openings 8. Reductive Ring Openings, Synthesis of a Subunit of Ionomycin 9. Reactivity of Silyl Nucleophiles 10. Conclusions and Future Studies

      >