495-20-5Relevant articles and documents
Ether-directed, stereoselective aza-claisen rearrangements: Synthesis of the piperidine alkaloid, α-conhydrine
Jamieson, Andrew G.,Sutherland, Andrew
, p. 1609 - 1611 (2007)
Equation presented A new approach for the stereoselective synthesis of the piperidine alkaloid (+)-α-conhydrine and its pyrrolidine derivative has been developed using a palladium(II)-catalyzed, MOM-ether-directed aza-Claisen rearrangement and ring-closing metathesis to effect the key steps.
Stereoselective addition of Grignard reagents to sulfinimines derived from tartrate diol (threitol): Generation of chiral building blocks for the collective total synthesis of lentiginosine, conhydrine and methyldihydropalustramate
Prasad, Kavirayani R.,Rangari, Vipin Ashok
, (2019/08/20)
A systematic investigation of the addition of Grignard reagents to sulfinimines derived from tartaric acid diol was undertaken. It was observed that the chirality of the inherent tartrate moiety influences the diastereoselectivity of the resultant sulfinamides formed in the reaction. The formed products serve as excellent building blocks for the synthesis of natural products. This has been demonstrated in the collective total synthesis of lentiginosine, (+)-α-conhydrine and methyldihydropalustramate.
Stereoselective total synthesis of (-)-β-conhydrine and (+)-α-conhydrine
Reyes, Efraim,Ruiz, Nerea,Vicario, Jose L.,Badia, Dolores,Carrillo, Luisa
, p. 443 - 450 (2011/04/16)
We have carried out the stereoselective synthesis of (-)-β- conhydrine and (+)-α-conhydrine, two bioactive α-hydroxyalkyl-substituted piperidines, using the commercially available and inexpensive amino alcohol (S,S)-(+)-pseudoephedrine as chiral auxiliary. The key step of this synthesis relies on new methodology previously developed in our group, consisting of the chemo- and diastereoselective addition of Grignard reagents across the C=N bond of α-iminoglyoxylamides derived from (S,S)-(+)-pseudoephedrine followed by the selective monoaddition of organolithium reagents to the carbamoyl group, leading to the formation of enantioenriched -amino ketones. Georg Thieme Verlag Stuttgart New York.
Enantioselective Synthesis of (+)-α-Conhydrine and (-)-Sedamine by L-ProlineCatalysed α-Aminooxylation
Shaikh, Tanveer Mahamadali,Sudalai, Arumugam
experimental part, p. 3437 - 3444 (2010/08/20)
An efficient organocatalytic approach to the enantioslective synthesis of two important piperidine alkaloids, namely (+)α-conhydrine (98% ee) and (-)-sedamine (95 % ee), by L-pro-line-catalysed α-aminooxylation of aldehydes has been developed. The strategy involves an intramolecular cyclization to construct the piperidine core.