41447-16-9Relevant academic research and scientific papers
Synthesis of bicyclic carbamates as precursors of Sedum alkaloid derivatives
Szakonyi, Zsolt,D'Hooghe, Matthias,Kanizsai, Iván,Fül?p, Ferenc,De Kimpe, Norbert
, p. 1595 - 1602 (2007/10/03)
Synthesis of a N-Boc-protected piperidin-2-yl phosphine oxide starting from piperidine in three steps, followed by olefination using a variety of α,β-unsaturated aldehydes resulted in tert-butyl 2-(2′- alkenylidene)piperidine-1-carboxylates in high yields
Short enantioselective synthesis of sedridines, ethylnorlobelols and coniine via reagent-based differentiation
Passarella, Daniele,Barilli, Alessio,Belinghieri, Francesca,Fassi, Paola,Riva, Sergio,Sacchetti, Alessandro,Silvani, Alessandra,Danieli, Bruno
, p. 2225 - 2229 (2007/10/03)
The preparation of collections of structurally diverse small molecules is a useful tool for studying biology and medicine with chemistry. Herein, we demonstrate the versatility of the pure enantiomers of 2-(2-oxo-ethyl)- piperidine-1-carboxylic acid tert-butyl ester to prepare the biological active alkaloids sedridine, allosedridine, methylsedridine, methylallosedridine, ethylnorlobelol, and coniine in two steps and in a stereoselective way via a reagent-based differentiation. The described syntheses are a demonstration of the versatility of 2-(2-oxo-ethyl)-piperidine-1-carboxylic acid tert-butyl esters as chiral building blocks.
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
