Pyrrolizidine synthesis via N-chloroamine rearrangements

Author

Paul Randall Williams

Date of Award

8-1982

Degree Type

Dissertation

Degree Name

Doctor of Philosophy

Major

Chemistry

Major Professor

Fred M. Schell

Abstract

A model system was investigated for its potential applicability toward pyrrolizidine diol synthesis via silver ion induced rearrangement of appropriately substituted N-chloroazabicyclo[4.2.0]-octanes. The results clearly show that this synthetic route is possible.

Attendant to this work was the demonstration that stereospecific modification of a single bicyclic ketoester into a series of diols of differing stereochemistries could be accomplished in high yield. Analogous treatment of compounds with the appropriate regiochemical and stereochemical relationships should provide the naturally occurring necine bases upon rearrangement. That systems of this type are available synthetically was also demonstrated.

Recommended Citation

Williams, Paul Randall, "Pyrrolizidine synthesis via N-chloroamine rearrangements. " PhD diss., University of Tennessee, 1982.
https://trace.tennessee.edu/utk_graddiss/13350