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Novel radical based routes to pyrrolidine trans-lactams

Novel radical based routes to pyrrolidine trans-lactams
Novel radical based routes to pyrrolidine trans-lactams

This thesis is concerned with the development of novel routes to the pyrrolidine trans-lactams 246, which proved to be HNE inhibitors, based on a radical cyclisation mediated by either samarium diiodide or tributyltin hydride. Chapter 2 describes the synthesis of precursors 214 and the radical cyclisation of a-aza radicals derived from N-(benzotriazolylalkyl) alkenylamines 264 mediated by samarium diiodide to access the trans-2,3-disubstituted pyrrolidines 267. After these results, the development of the synthetic route of pyrrolidine trans-lactam was described. The cyclisation of the pyrrolidine derivative 245 successfully gave pyrrolidine trans-lactam 253.

University of Southampton
Ajavakom, Anawat
5bfbc657-18ac-4cfd-8e6c-3969f2a51e0e
Ajavakom, Anawat
5bfbc657-18ac-4cfd-8e6c-3969f2a51e0e

Ajavakom, Anawat (2003) Novel radical based routes to pyrrolidine trans-lactams. University of Southampton, Doctoral Thesis.

Record type: Thesis (Doctoral)

Abstract

This thesis is concerned with the development of novel routes to the pyrrolidine trans-lactams 246, which proved to be HNE inhibitors, based on a radical cyclisation mediated by either samarium diiodide or tributyltin hydride. Chapter 2 describes the synthesis of precursors 214 and the radical cyclisation of a-aza radicals derived from N-(benzotriazolylalkyl) alkenylamines 264 mediated by samarium diiodide to access the trans-2,3-disubstituted pyrrolidines 267. After these results, the development of the synthetic route of pyrrolidine trans-lactam was described. The cyclisation of the pyrrolidine derivative 245 successfully gave pyrrolidine trans-lactam 253.

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Published date: 2003

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Local EPrints ID: 465083
URI: http://eprints.soton.ac.uk/id/eprint/465083
PURE UUID: a2a3fd94-aac2-47c5-aa47-cb186f4d61a9

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Date deposited: 05 Jul 2022 00:22
Last modified: 05 Jul 2022 04:10

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Author: Anawat Ajavakom

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