Multicomponent linchpin coupling of silyl dithianes employing an N-Ts aziridine as the second electrophile: synthesis of (-)-indolizidine 223AB.
[reaction: see text] An efficient, stereocontrolled assembly of the indolizidine alkaloid, (-)-indolizidine 223AB, exploiting a three-component linchpin coupling employing an N-Ts aziridine as the second electrophile, followed by a one-pot sequential construction of the indolizidine ring system, has been achieved. The longest linear sequence was 10 steps, proceeding in 10% overall yield.
Smith
Amos B
AB
Department of Chemistry, Monell Chemical Senses Center and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. smithab@sas.upenn.edu
Kim
Dae-Shik
DS
D001388:Aziridines / Q000737:chemistry*; D007212:Indolizines / Q000138:chemical synthesis*; D008968:Molecular Conformation; D011807:Quinolizines / Q000737:chemistry*; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000737:chemistry*
D001388:Aziridines; D007212:Indolizines; D011807:Quinolizines; D013457:Sulfur Compounds; C438055:dithiane; C413142:indolizidine 223AB; C033132:aziridine