160798-30-1Relevant academic research and scientific papers
Redox-Neutral α-C-H Functionalization of Pyrrolidin-3-ol
Yi, Cheng-Bo,She, Zhi-Ying,Cheng, Yong-Feng,Qu, Jin
supporting information, p. 668 - 671 (2018/02/09)
A redox-neutral α-C-H oxygenation of commercially available pyrrolidin-3-ol with a monoprotected p-quinone generated an N-aryliminium ion intermediate, which reacted in situ with boronic acid nucleophiles to produce a series of cis-2-substituted pyrrolidin-3-ols. With this strategy, 8-epi-(-)-lentiginosine was synthesized from (3R,4R)-pyrrolidine-3,4-diol in three steps.
Synthesis of hydroxylated pyrrolidines by allenic cyclisation
Ng, Pearly Shuyi,Bates, Roderick W.
, p. 6356 - 6362 (2016/09/23)
The diastereoselective gold(I) catalysed cyclisation of highly substituted aminoallene derivatives allows the synthesis of both epi-DAB-1 and di-epi-lentiginosine. While the sense of stereoselectivity observed is in line with earlier observations on analo
Structure-guided engineering of D-fructose-6-phosphate aldolase for improved acceptor tolerance in biocatalytic aldol additions
Soler, Anna,Gutiérrez, Mariana L.,Bujons, Jordi,Parella, Teodor,Minguillon, Cristina,Joglar, Jesús,Clapés, Pere
, p. 1787 - 1807 (2015/06/02)
Abstract A structure-guided redesign of D-fructose-6-phosphate aldolase from Escherichia coli (FSA) was devised for improving the acceptor tolerance towards α-substituted and conformationally constrained aldehydes. FSA A129S/R134X/A165G/S166G and L107Y/A1
Synthesis of pyrrolidine iminosugars, (-)-lentiginosine, (-)-swainsonine and their 8a-epimers from d-glycals
Ansari, Alafia A.,Vankar
, p. 12555 - 12567 (2014/03/21)
Synthesis of pyrrolidine iminosugars has been described from d-glycals via dihydroxylation, oxidative cleavage and double nucleophilic displacement as the key steps. The pyrrolidines obtained have been utilized for the synthesis of important bicyclic iminosugars, viz. (-)-lentiginosine and (-)-swainsonine and their 8a-epimers, which are known to be glycosidase inhibitors.
Efficient synthesis of (+)-1,8,8a-tri-epi-swainsonine, (+)-1,2-di-epi- lentiginosine, (+)-9a-epi-homocastanospermine and (-)-9-deoxy-9a-epi- homocastanospermine from a d-glucose-derived aziridine carboxylate, and study of their glycosidase inhibitory activities
Ajish Kumar,Chaudhari, Vinod D.,Dhavale, Dilip D.
, p. XX703-711 (2008/09/17)
The utility of a d-glucose-derived aziridine carboxylate was demonstrated for the synthesis of polyhydroxylated quinolizidine and indolizidine alkaloids. The chemoselective reduction of 1 followed by two-carbon homologation by the Wittig reaction afforded γ,δ-aziridino-α,β-unsaturated ester 9, which on regioselective nucleophilic aziridine ring opening either by using water as a nucleophile or hydrogenation afforded δ-lactams 11/16-true synthons for the synthesis of four structurally different iminosugars, namely quinolizidine alkaloids 5b/5c, swainsonine 6b and lentiginosine 7b analogues. Glycosidase inhibitory activities of these iminosugars were investigated. This journal is The Royal Society of Chemistry.
A concise synthesis of lentiginosine derivatives using a pyridinium formation via the Mitsunobu reaction
Azzouz, Rabah,Fruit, Corinne,Bischoff, Laurent,Marsais, Francis
, p. 1154 - 1157 (2008/09/18)
(Chemical Equation Presented) A four-step synthesis of (-)-lentiginosine and its epimers is described starting from 2-bromopyridine. The key step consisted of a quaternarization of a fully unprotected pyridinium-polyol unit using Mitsunobu methodology. Su
Synthesis of (-)-lentiginosine, its 8a-epimer and dihydroxylated pyrrolizidine alkaloid from d-glucose
Chaudhari, Vinod D.,Ajish Kumar,Dhavale, Dilip D.
, p. 4349 - 4354 (2007/10/03)
The d-glucose derived α,β-unsaturated ester 5 on 1,2-acetonide deprotection, oxidative diol cleavage followed by treatment with N-benzylamine in the presence of NaBH3CN undergoes reductive amination and a concomitant intramolecular conjugate ad
