67217-85-0Relevant articles and documents
Cross-coupling of cyclopropanols: Concise syntheses of indolizidine 223AB and congeners
Rao, Nagavaram Narsimha,Parida, Bibhuti Bhusan,Cha, Jin Kun
, p. 6208 - 6211 (2014)
A new synthetic method for indolizidine or pyrrolizidine alkaloids based on readily available and attractively functionalized cyclopropanols, as exemplified in concise syntheses of indolizidine (-)-223AB, its 3-epimer, (-)-indolizidine 239AB, and (-)-indolizidine 239CD, is reported. This work highlights the applications of SN2′ alkylation and C-acylation of cyclopropanols to meet stereochemical challenges in natural product synthesis. Also included is diastereoselective cyclization of the resulting aminoallene adduct for bicyclic ring formation.
Enantiopure 2,6-disubstituted piperidines bearing one alkene- or alkyne-containing substituent: Preparation and application to total syntheses of indolizidine-alkaloids
Liu, Hui,Su, Deyong,Cheng, Guolin,Xu, Jimin,Wang, Xinyan,Hu, Yuefei
supporting information; experimental part, p. 1899 - 1904 (2010/08/21)
A general and efficient procedure for the preparation of 2,6-disubstituted piperidines bearing one alkene- or alkyne-containing substituent was developed by using non-racemic Betti base as a chiral auxiliary. Many chiral benzylamines are excellent auxiliaries, but they were rarely used for this purpose because of the inefficient removal of the N-benzyl auxiliary residue under non-hydrogenative conditions. We found that N,N-disubstituted Betti base derivative has a typical Mannich structure of o-naphthol. When it carried out a base-catalyzed formation of o-quinone methide, an efficient non-hydrogenative N-debenzylation was achieved, and the alkene and alkyne groups survived. To demonstrate the efficiency of the method and the versatility of the products, asymmetric total syntheses of indolizidine-alkaloids (-)-167B, (-)-195H, (-)-209D and (-)-223AB were accomplished.
Asymmetric synthesis of 3,5-disubstituted indolizidines by intermolecular addition of an allylsilane on an N-acyliminium ion
Conchon, Elisabeth,Gelas-Mialhe, Yvonne,Remuson, Roland
, p. 1253 - 1257 (2007/10/03)
A diastereoselective synthesis of 3,5-disubstituted indolizidines based on an intermolecular addition of an allylsilane on an acyliminium ion derived from (S)-pyroglutamic acid is described. The synthetic potential of this methodology is demonstrated by t