Intramolecular Diels-Alder and tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition reactions of 1,3,4-oxadiazoles.
The scope of intramolecular Diels-Alder and a novel tandem Diels-Alder/1,3-dipolar cycloaddition cascade of 1,3,4-oxadiazoles is disclosed. In the cases examined, the tandem cycloadditions construct three new rings with formation of four new C-C bonds and set all six stereocenters about a central six-membered ring in a single step including three contiguous and four total quaternary centers without a trace of a second diastereomer.
Wilkie
Gordon D
GD
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Elliott
Gregory I
GI
Blagg
Brian S J
BS
Wolkenberg
Scott E
SE
Soenen
Danielle R
DR
Miller
Michael M
MM
Pollack
Scott
S
Boger
Dale L
DL
D003500:Cyclization; D010069:Oxadiazoles / Q000737:chemistry*; D014747:Vinblastine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
D010069:Oxadiazoles; C009667:vindoline; D014747:Vinblastine