Asymmetric synthesis of unsaturated monocyclic and bicyclic nitrogen heterocycles

Nomura, Hiroshi and Richards, Christopher J. (2009) Asymmetric synthesis of unsaturated monocyclic and bicyclic nitrogen heterocycles. Organic Letters, 11 (13). pp. 2892-2895.

[img]
Preview
PDF (OL09-11-2892) - Accepted Version
Available under License Unspecified licence.

Download (217kB) | Preview

Abstract

Hydrolysis of scalemic trichloroacetamides Cl3CCONHCH(R)CHCH2 and allylation, or acylation with but-3-enoic acid, followed by ring-closing metathesis resulted in the formation of unsaturated pyrrolidine and piperidine building blocks. These were employed in the synthesis of (S)-coniine (R = Pr) and a formal synthesis of (+)-anisomycin (R = p-MeOC6H4). Extension of this methodology with R = CH2CHCH2 employing two ring-closing metatheses resulted in the synthesis of unsaturated quinolizidinone and indolizidinone frameworks.

Item Type: Article
Faculty \ School: Faculty of Science > School of Chemistry
Related URLs:
Depositing User: Rachel Smith
Date Deposited: 29 Mar 2011 10:42
Last Modified: 24 May 2022 12:16
URI: https://ueaeprints.uea.ac.uk/id/eprint/27397
DOI: 10.1021/ol900880w

Actions (login required)

View Item View Item