seco-C/D ring analogues of ergot alkaloids. Synthesis via intramolecular Heck and ring-closing metathesis reactions.
[reaction: see text] Intramolecular Heck and ring-closing metathesis reactions on key intermediates 10 and 15, respectively, provide efficient entries into seco-C/D ring analogues of Ergot alkaloids 12 and 16, compounds of potential synthetic and biological interest.
Kalinin
Alexey V
AV
Department of Chemistry, University of Waterloo, Waterloo, Ontario, Canada N2L 3G1.
Chauder
Brian A
BA
Rakhit
Suman
S
Snieckus
Victor
V
D000316:Adrenergic alpha-Agonists / Q000138:chemical synthesis; D003500:Cyclization; D004873:Ergolines / Q000138:chemical synthesis; D004876:Ergot Alkaloids / Q000138:chemical synthesis*; D006572:Heterocyclic Compounds, Bridged-Ring / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000316:Adrenergic alpha-Agonists; D004873:Ergolines; D004876:Ergot Alkaloids; D006572:Heterocyclic Compounds, Bridged-Ring