Total synthesis of (+/-)-powelline and (+/-)-buphanidrine.
The total synthesis of (+/-)-powelline (13 linear steps in an overall yield of 6%) and (+/-)-buphanidrine (14 linear steps and a 6% overall yield) and has been achieved using a novel approach to the crinane skeleton. An organocatalytic oxidative coupling allowed direct construction of the key quaternary carbon-to-aryl bond in high yield allowing rapid access to the target alkaloids.
Bogle
Katherine M
KM
School of Chemistry, The University of Manchester, Oxford Road, Manchester M13 9PL, UK.
Hirst
David J
DJ
Dixon
Darren J
DJ
D047151:Amaryllidaceae Alkaloids; D018360:Crystallography, X-Ray; D019668:Liliaceae / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010617:Phenanthridines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D047151:Amaryllidaceae Alkaloids; D010617:Phenanthridines; C549992:buphanidrine; C549991:powelline