Total syntheses of (±)-securinine and (±)- allosecurinine.
Total syntheses of (±)-securinine and (±)-allosecurinine that employ a tandem rhodium carbenoid-initiated Claisen/α-ketol rearrangement sequence as a key step are described.
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Jung-Hsuan
JH
Chen
Samantha R
SR
Levine
Jonas F
JF
Buergler
Travis C
TC
McMahon
Matthew R
MR
Medeiros
John L
JL
Wood
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D019665:Euphorbiaceae / Q000737:chemistry; D006572:Heterocyclic Compounds, Bridged-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D001381:Azepines; D006572:Heterocyclic Compounds, Bridged-Ring; D007783:Lactones; D010880:Piperidines; D012238:Rhodium; C000785:securinine