Total synthesis of the lycorenine-type amaryllidaceae alkaloid (+/-)-clivonine via a biomimetic ring-switch from a lycorine-type progenitor.
A fully diastereoselective total synthesis of the lycorenine-type Amaryllidaceae alkaloid (+/-)-clivonine (19) is reported via a route that employs for the first time a biomimetic ring-switch from a lycorine-type progenitor, thereby corroborating experimentally the biogenetic hypothesis first expounded for these compounds by Barton in 1960.
Giró Mañas
Carles
C
Department of Chemistry, South Kensington Campus, Imperial College London, London SW7 2AZ, UK.
Paddock
Victoria L
VL
Bochet
Christian G
CG
Spivey
Alan C
AC
White
Andrew J P
AJ
Mann
Inderjit
I
Oppolzer
Wolfgang
W
D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D010617:Phenanthridines / Q000737:chemistry*; D013237:Stereoisomerism
D047151:Amaryllidaceae Alkaloids; D010617:Phenanthridines; C550290:clivonine; C023825:lycorenine; C015330:lycorine