An Ammonia‐Triggered Stereocontrolled Conversion of a γ‐Lactone to the Central Tetrahydropyran of Pederin, Psymberin, and Onnamides D–F | Zendy

Buffham William J. | Zendy; Swain Nigel A. | Zendy; Kostiuk Sarah L. | Zendy; Gonçalves Théo P. | Zendy; Harrowven David C. | Zendy

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An Ammonia‐Triggered Stereocontrolled Conversion of a γ‐Lactone to the Central Tetrahydropyran of Pederin, Psymberin, and Onnamides D–F

Author(s) -

Buffham William J.,

Swain Nigel A.,

Kostiuk Sarah L.,

Gonçalves Théo P.,

Harrowven David C.

Publication year - 2012

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201101543

Subject(s) - tetrahydropyran , chemistry , lactone , stereochemistry , sequence (biology) , ring (chemistry) , malic acid , ammonia , combinatorial chemistry , organic chemistry , biochemistry , citric acid

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 γ‐lactone to a tetrahydropyran structure triggered by the addition of ammonia.

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