Total synthesis of anhydrolycorinone utilizing sequential intramolecular Diels-Alder reactions of a 1,3,4-oxadiazole.
A convergent total synthesis of anhydrolycorinone is detailed, enlisting sequential intramolecular Diels-Alder reactions of a suitably substituted 2-amino-1,3,4-oxadiazole defining a novel oxadiazole --> furan --> benzene Diels-Alder strategy.
Wolkenberg
Scott E
SE
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Boger
Dale L
DL
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D047151:Amaryllidaceae Alkaloids; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D010069:Oxadiazoles; D010617:Phenanthridines / Q000138:chemical synthesis* / Q000737:chemistry*
D000470:Alkaloids; D047151:Amaryllidaceae Alkaloids; D007202:Indicators and Reagents; D010069:Oxadiazoles; D010617:Phenanthridines; C420562:anhydrolycorinone; C015330:lycorine