Nonstabilized N-unsubstituted azomethine ylides: a synthesis of indolizidine 239CD.
[formula: see text] Treatment of a (2-azaallyl)stannane with HF.pyridine generated a nonstabilized N-unsubstituted azomethine ylide, which was found to undergo an efficient and stereoselective dipolar cycloaddition with phenyl vinyl sulfone to produce a trans-2,5-dialkylpyrrolidine that was further transformed into the dendrobatid alkaloid indolizidine 239CD.
Clark
R B
RB
Department of Chemistry, University of Michigan, Ann Arbor 48109-1055, USA.
Pearson
W H
WH
D000818:Animals; D000832:Animals, Poisonous; D001001:Anura; D007212:Indolizines / Q000138:chemical synthesis*
D007212:Indolizines; C410457:indolizidine 239CD