Tricyclic alkaloid core structures assembled by a cyclotrimerization-coupled intramolecular nucleophilic substitution reaction.
A facile approach to tricyclic alkaloid core structures was developed by sequencing a pyridine-forming [2 + 2 + 2] cyclotrimerization reaction with an intramolecular nucleophilic substitution. This methodology enabled the facile assembly of the spiroindolinone framework of citrinadins A and B, and cyclopiamine B.
McIver
Andrew L
AL
North Carolina State University, Department of Chemistry, Raleigh, North Carolina 27695-8204, USA.
Deiters
Alexander
A
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D008872:Microwaves; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D011725:Pyridines; C023666:pyridine