89772-92-9Relevant articles and documents
Convergent asymmetric synthesis of indolizidines from (S)-5-(tosylmethyl)-2-pyrrolidinone: Synthesis of (-)-δ-coniceine
Costa, Ana,Najera, Carmen,Sansano, Jose M.
, p. 2205 - 2211 (2007/10/03)
The enantiomerically pure (S)-5-(tosylmethyl)-2-pyrrolidinone 2, prepared from commercially available (S)-pyroglutaminol, is dialkylated at the nitrogen atom and the α-sulfonyl position using several dielectrophiles using sodium hydride as the base to diastereoselectively afford indolizidine derivatives 5 and the less common hexahydropyrrolo[1,2-a]azepin-3-one 6 in moderate to good yield. This domino process has been applied to the synthesis of (-)-δ-coniceine.
Optical Rotatory Dispersion and Absolute Configuration. Part 35. Chiroptical Properties and Conformation of Indolizidine
Ringdahl, Bjorn,Pinder, A. Reginald,Pereira, Wilfred E.,Oppenheimer, Norman J.,Craig, John Cymerman
, p. 1 - 4 (2007/10/02)
1H N.m.r. spectroscopy at 360 MHz confirms that indolizidine is trans-fused with the piperidine ring in a chair conformation.The pyrrolidine ring adopts an envelope conformation with the nitrogen atom displaced out of the plane of the four carbon atoms of the ring.An improved synthesis of (+)- and (-)-indolizidine from (-)- and (+)-coniine is described.The o.r.d. and c.d. spectra of indolizidine are compared with those of coniine.
