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An ammonia-triggered stereocontrolled conversion of a ?-lactone to the central tetrahydropyran of pederin, psymberin, and onnamides D-F

An ammonia-triggered stereocontrolled conversion of a ?-lactone to the central tetrahydropyran of pederin, psymberin, and onnamides D-F
An ammonia-triggered stereocontrolled conversion of a ?-lactone to the central tetrahydropyran of pederin, psymberin, and onnamides D-F
The onnamides, pederin, and psymberin have each attracted attention because of their potent biological activity and interesting structural features. A short (eight steps) and efficient stereocontrolled route to the central tetrahydropyran ring in these natural products has been developed from (S)-malic acid. The key sequence involves the conversion of a ?-lactone to a tetrahydropyran structure triggered by the addition of ammonia.
lactones, oxygen heterocycles, ring expansion, cyclization, synthesis design
1434-193X
1217-1222
Buffham, William J.
e8cbab6d-d481-4b1a-9015-db6a382c3a38
Swain, Nigel A.
522cad04-7679-4f30-9b4a-c4351017edad
Kostiuk, Sarah L.
dc9687f9-d644-4540-be20-cc992002450f
Gonçalves, Théo P.
bf763652-dc7b-4f8e-9cc2-6be930274533
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Buffham, William J.
e8cbab6d-d481-4b1a-9015-db6a382c3a38
Swain, Nigel A.
522cad04-7679-4f30-9b4a-c4351017edad
Kostiuk, Sarah L.
dc9687f9-d644-4540-be20-cc992002450f
Gonçalves, Théo P.
bf763652-dc7b-4f8e-9cc2-6be930274533
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b

Buffham, William J., Swain, Nigel A., Kostiuk, Sarah L., Gonçalves, Théo P. and Harrowven, David C. (2012) An ammonia-triggered stereocontrolled conversion of a ?-lactone to the central tetrahydropyran of pederin, psymberin, and onnamides D-F. European Journal of Organic Chemistry, 2012 (6), 1217-1222. (doi:10.1002/ejoc.201101543).

Record type: Article

Abstract

The onnamides, pederin, and psymberin have each attracted attention because of their potent biological activity and interesting structural features. A short (eight steps) and efficient stereocontrolled route to the central tetrahydropyran ring in these natural products has been developed from (S)-malic acid. The key sequence involves the conversion of a ?-lactone to a tetrahydropyran structure triggered by the addition of ammonia.

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More information

Published date: February 2012
Keywords: lactones, oxygen heterocycles, ring expansion, cyclization, synthesis design
Organisations: Chemistry

Identifiers

Local EPrints ID: 337262
URI: https://eprints.soton.ac.uk/id/eprint/337262
ISSN: 1434-193X
PURE UUID: 32707a71-d3cc-4eba-9097-42e0eaa96105
ORCID for David C. Harrowven: ORCID iD orcid.org/0000-0001-6730-3573

Catalogue record

Date deposited: 20 Apr 2012 12:03
Last modified: 19 Nov 2019 01:59

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