A new entry to Amaryllidaceae alkaloids from carbohydrates: total synthesis of (+)-vittatine.
The stereoselective and chiral synthesis of the Amaryllidaceae alkaloid, (+)-vittatine 1, is described; the quaternary carbon in 1 was generated by Claisen rearrangement of a cyclohexenol derived from D-glucose by way of a Ferrier's carbocyclisation reaction and a hexahydroindole skeleton was effectively constructed by intramolecular aminomercuration-demercuration, followed by Chugaev reaction.
Bohno
Masahiro
M
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
Imase
Hidetomo
H
Chida
Noritaka
N
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D010617:Phenanthridines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D002241:Carbohydrates; D010617:Phenanthridines; C488939:vittatine 1