Asymmetric synthesis of unsaturated monocyclic and bicyclic nitrogen heterocycles

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Nomura, Hiroshi and Richards, Christopher J. (2009) Asymmetric synthesis of unsaturated monocyclic and bicyclic nitrogen heterocycles. Organic Letters, 11 (13). pp. 2892-2895. ISSN 1523-7052

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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 (former - to 2024)
UEA Research Groups:	Faculty of Science > Research Groups > Chemistry of Materials and Catalysis Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017)
Related URLs:	http://dx.doi.org/10.1021/ol900880w
Depositing User:	Rachel Smith
Date Deposited:	29 Mar 2011 10:42
Last Modified:	06 Feb 2025 02:20
URI:	https://ueaeprints.uea.ac.uk/id/eprint/27397
DOI:	10.1021/ol900880w

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