A formal synthesis of (-)-cephalotaxine.
An enantioselective formal synthesis of the alkaloid (-)-cephalotaxine has been completed, using an alkylidene carbene 1,5-CH insertion reaction as a key step to construct the spiro[4.4]azanonane core D/E-ring system. A Heck-type cyclization was used to close the tetrahydroazepine C-ring and a selective epoxidation-rearrangement sequence was used to elaborate the E-ring.
Esmieu
William R
WR
School of Chemistry, University of Nottingham, Nottingham, UK.
Worden
Stephen M
SM
Catterick
David
D
Wilson
Claire
C
Hayes
Christopher J
CJ
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D006248:Harringtonines / Q000138:chemical synthesis* / Q000737:chemistry; D000077863:Homoharringtonine; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
D000470:Alkaloids; D006248:Harringtonines; D000077863:Homoharringtonine