Caged trans-4-hydroxy-2-nonenal.
[reaction: see text] A caged 4-hydroxy-2-nonenal (4-HNE) has been prepared and its photochemistry investigated. Upon photolysis, 1 releases 4-HNE in up to 100% yield. From these photolyses, 4-HNE could be isolated in up to 91% yield. 4-HNE is produced under either aerobic or anaerobic conditions. The caging strategy does not require prior preparation of 4-HNE and, therefore, represents a three-step synthetic route to the bioactive enal in 48% overall yield.
Brinson
Robert G
RG
Department of Chemistry, Wake Forest University, Winston-Salem, North Carolina 27109, USA.
Jones
Paul B
PB
D000447:Aldehydes / Q000737:chemistry*; D010777:Photochemistry; D013056:Spectrophotometry, Ultraviolet
D000447:Aldehydes; C027576:4-hydroxy-2-nonenal