Total synthesis of (-)-stemonine.
[reaction: see text] An enantioselective total synthesis of (-)-stemonine (1) is reported via a convergent assembly of the acyclic precursor 2. Key transformations include a Staudinger-aza-Wittig reaction to form the central perhydroazepine ring system and an iodine-induced tandem cyclization to construct the pyrrolidino-butyrolactone framework.
Williams
David R
DR
Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405-7102, USA. williamd@indiana.edu
Shamim
Khalida
K
Reddy
Jayachandra P
JP
Amato
George S
GS
Shaw
Stephen M
SM
D000470:Alkaloids / Q000138:chemical synthesis*; D001381:Azepines / Q000737:chemistry; D003500:Cyclization; D007455:Iodine / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D041901:Stemonaceae / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D001381:Azepines; D007783:Lactones; D011759:Pyrrolidines; C483261:stemonine; D007455:Iodine; C048618:hexahydroazepine