Synthetic applications of the aza-Achmatowicz rearrangement

A novel method for the enantioselective synthesis of nitrogen containing compounds has been achieved. The oxidative rearrangement of N-acyl 2-furylamines, termed the Aza-Achmatowicz rearrangement, generates a product with a high density of differentiable functionalities. This characteristic of the product makes it an excellent building block for the synthesis of nitrogenous substances of biomedical interest. Optically pure building blocks are also available via the Aza-Achmatowicz rearrangement. The generation of chirality in the starting furyl derivative is obtained by a simple, inexpensive chemoenzymatic method utilizing papain. The chemical reactivity of these heterocycles has been thoroughly explored, and utilized in the synthesis of (+)-desoxoprosopinine, deoxyazasaccharides, izidinie alkaloid systems, β-lactams, and unusual amino acids.

Name thesis:degree_name

Doctor of Philosophy

Level thesis:degree_level

Doctoral

Discipline thesis:degree_discipline

Natural Sciences

Grantor

Rice University

Year dc:date.issued

1990

Author dc:creator

• Hermann, Cynthia Wood

Advisor dc:contributor.advisor

• Ciufolini, Marco A.

• Organic chemistry

Statement dc:rights

• Copyright is held by the author, unless otherwise indicated. Permission to reuse, publish, or reproduce the work beyond the bounds of fair use or other exemptions to copyright law must be obtained from the copyright holder.

Language dc:language.iso

eng

Handle dc:identifier.uri

https://hdl.handle.net/1911/16348

OAI identifier oai:identifier

oai:repository.rice.edu:1911/16348