190383-64-3Relevant academic research and scientific papers
Protecting-Group-Directed Regio- and Stereoselective Oxymercuration-Demercuration: Synthesis of Piperidine Alkaloids Containing 1,2- and 1,3-Amino Alcohol Units
Bugde, Sandesh T.,Volvoikar, Prajesh S.,Tilve, Santosh G.
, p. 1113 - 1122 (2017/12/06)
An efficient synthesis of naturally occurring 1,2- and 1,3-amino alcohol unit containing 2-substituted piperidine alkaloids and their analogues has been developed from l -pipecolinic acid. The protocol describes the regio- and stereoselective oxymercuration-demercuration of 2-alkenyl piperidines based on protecting groups to give piperidine alkaloids as a key step.
Synthetic studies of alkaloids containing pyrrolidine and piperidine structural motifs
Bhat, Chinmay
, p. 192 - 196 (2015/04/27)
Avenues to asymmetric alkaloids! Various 2-substituted pyrrolidine and piperidine chiral bioactive natural products were synthesized using a 'chiral pool' method. l-proline and l-pipecolinic acids with one chiral center served as the best precursors for the synthesis of these alkaloids. Overall, 14 total synthetic and 11 formal synthetic approaches were developed.
Henry-Nef reaction: A practical and versatile chiral pool route to 2-substituted pyrrolidine and piperidine alkaloids
Bhat, Chinmay,Tilve, Santosh G.
, p. 6129 - 6143 (2013/07/27)
The paper describes the synergistic protocol developed by combinatorial Henry and Nef reaction for the synthesis of 2-substituted pyrrolidine and piperidine alkaloids containing 1,3-aminoketone and 1,3-amino alcohol units. The utility of the protocol is demonstrated by asymmetric synthesis of 12 natural products of which asymmetric synthesis of (-)-N-methylpelletierine is presented for the first time. The one-carbon homologation described also provides an alternate route for the synthesis of key intermediates homoprolinol and homopipecolinol used as synthetic precursors for several alkaloids and construction of β-amino acids from α-amino acids.
A new synthesis of all four stereoisomers of 2-(2,3- dihydroxypropyl)piperidine via iterative asymmetric dihydroxylation to cause enantiomeric enhancement. Application to asymmetric synthesis of naturally occurring piperidine-related alkaloids
Takahata, Hiroki,Kubota, Minoru,Ikota, Nobuo
, p. 8594 - 8601 (2007/10/03)
Both enantiomers of 2-(2-propenyl)piperidine 1 (76-88% ee), prepared via the first asymmetric dihydroxylation (AD) of 5-hexenyl azide, underwent the second AD to provide all four of the stereoisomeric 2-(2,3- dihydroxypropyl)piperidines 2 with enantiomeric enhancement.(>98% ee). An asymmetric synthesis, starting from 2, of several 2-(2- hydroxyalkyl)piperidine alkaloids [(-)halosaline, (+)-N-methylallosedridine, (+)-8-ethylnorlobelol, (+)-sedridine, (+)-allosedridine, (-)allosedridine, and (+)-N-methylsedridine] and the ant defense alkaloids [(+)-tetraponerine-3 (T-3), T-4, T-7, and T-8] is demonstrated.
A general entry to 2-(2-hydroxyalkyl)piperidines via iterative asymmetric dihydroxylation to cause enantiomeric enhancement
Takahata, Hiroki,Kubota, Minoru,Momose, Takefumi
, p. 3451 - 3454 (2007/10/03)
Both enantiomers of 2-(2-propenyl)piperidine (1) (76-88% ee), prepared via the first AD of 5-hexenyl azide, underwent the second AD to provide all of the four stereoisomeric 2-(2-hydroxypropyl)piperidines (2) with enantiomeric enhancement (>98 ee). An asy
