Highly enantioselective total synthesis of (−)-(3′S)-lomatin and (+)-(3′S,4′R)-trans-khellactone

Bulman Page, Philip C., Appleby, Louise F., Day, David, Chan, Yohan, Buckley, Benjamin R., Allin, Steven M. and McKenzie, Michael J. (2009) Highly enantioselective total synthesis of (−)-(3′S)-lomatin and (+)-(3′S,4′R)-trans-khellactone. Organic Letters, 11 (9). pp. 1991-1993. ISSN 1523-7052

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Abstract

Concise highly enantioselective three-step syntheses are described for (-)-(3'S)-lomatin and (+)-(3'S,4'R)-trans-khellactone from 7-hydroxycoumarin in 97% ee and in 57% and 58% overall yields, respectively, using nonaqueous enantioselective epoxidation by an iminium salt as the key step.

Item Type:	Article
Faculty \ School:	Faculty of Science > School of Chemistry (former - to 2024)
UEA Research Groups:	Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017) Faculty of Science > Research Groups > Chemistry of Materials and Catalysis
Depositing User:	Rachel Smith
Date Deposited:	22 Mar 2011 12:21
Last Modified:	28 Mar 2025 03:14
URI:	https://ueaeprints.uea.ac.uk/id/eprint/26841
DOI:	10.1021/ol900444h

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