26171-47-1Relevant articles and documents
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 (2005)
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.
Total synthesis of sedum alkaloids via catalyst controlled aza-cope rearrangement and hydroformylation with formaldehyde
Ren, Hong,Wulff, William D.
supporting information, p. 242 - 245 (2013/03/28)
The catalytic asymmetric aminoallylation of chiral aldehydes is developed as a new method for the catalyst controlled synthesis of syn-and anti-1,3-aminoalcohols. This methodology is highlighted in the synthesis of the sedum alkaloids (+)-sedridine and (+)-allosedridine both of which have their final carbon incorporated during closure of the piperidine ring via a hydroformylation with formaldehyde.
Stereocontrol in N-directed hydroboration: Synthesis of amino alcohols related to the piperidine alkaloids
Wang, Guoqiang,Vedejs, Edwin
supporting information; experimental part, p. 1059 - 1061 (2009/08/15)
Treatment of 2-(2'-alkenyl)-piperidine boranes with iodine or triflic acid induces internal hydroboration with high regiocontrol, even with a terminal alkene (R H). Good stereocontrol is possible for the N-benzyl substrates. Comparisons with acyclic model
