A general, convergent strategy for the construction of indolizidine alkaloids: total syntheses of (-)-indolizidine 223AB and alkaloid (-)-205B.
N-Toluenesulfonyl aziridines comprise effective second electrophiles in the solvent controlled three-component linchpin union of silyl dithianes for the stereocontrolled convergent elaboration of protected 1,5-amino alcohols. This tactic, in conjunction with a one-flask sequential cyclization, constitutes an effective general strategy for the construction of indolizidine and related alkaloids, illustrated here with the total syntheses of (-)-indolizidine 223AB (1) and alkaloid (-)-205B (2).
Department of Chemistry, Monell Chemical Senses Center and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, PA 19104, USA. smithab@sas.upenn.edu
Amos B
AB
Smith
Dae-Shik
DS
Kim
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D000470:Alkaloids; D006575:Heterocyclic Compounds, 3-Ring; D007212:Indolizines; C510161:alkaloid (-)-205B; C413142:indolizidine 223AB