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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.