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.
Department of Chemistry, South Kensington Campus, Imperial College London, London SW7 2AZ, UK.
Carles
C
Giró Mañas
Victoria L
VL
Paddock
Christian G
CG
Bochet
Alan C
AC
Spivey
Andrew J P
AJ
White
Inderjit
I
Mann
Wolfgang
W
Oppolzer
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