A photochemical approach to the Galanthan ring system.
A five-step, atom-efficient synthesis of the Galanthan tetracyclic skeleton has been developed. The key step is an unusual intramolecular de Mayo reaction using an isocarbostyril substrate with a functionalized tether on nitrogen. The target molecule is produced in 35% overall yield from isocarbostyril.
Department of Chemistry, Texas Christian University, Fort Worth, Texas 76129, USA. d.minter@tcu.edu
David E
DE
Minter
Christopher D
CD
Winslow
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010617:Phenanthridines / Q000138:chemical synthesis* / Q000737:chemistry; D010777:Photochemistry
D000470:Alkaloids; D010617:Phenanthridines