Total synthesis of 7-deoxypancratistatin-1-carboxaldehyde and carboxylic acid via solvent-free intramolecular aziridine opening: phenanthrene to phenanthridone cyclization strategy.
Solid-state silica-gel-catalyzed opening of aziridine 6 provided phenanthrene 7, whose oxidative cleavage, recyclization, and further elaboration furnished the C-1 aldehyde and carboxylic acid derivatives of 7-deoxypancratistatin for potential analogue synthesis.
Collins
Jonathan
J
Department of Chemistry and Centre for Biotechnology, Brock University, 500 Glenridge Avenue, St. Catharines, Ontario L2S 3A1, Canada.
Drouin
Melissa
M
Sun
Xuetong
X
Rinner
Uwe
U
Hudlicky
Tomas
T
D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry*; D002264:Carboxylic Acids; D002384:Catalysis; D003500:Cyclization; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010616:Phenanthrenes / Q000737:chemistry*
C527909:7-deoxypancratistatin-1-carboxaldehyde; D047151:Amaryllidaceae Alkaloids; D001388:Aziridines; D002264:Carboxylic Acids; D007546:Isoquinolines; D010616:Phenanthrenes; C031181:phenanthrene; C033132:aziridine; C040601:phenanthridone