495-20-5Relevant academic research and scientific papers
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 syntheses of (+)-α- and (-)-β-conhydrine from L-aspartic acid
Pandey, Satyendra Kumar,Kumar, Pradeep
, p. 4091 - 4093 (2005)
An efficient synthesis of (+)-α-conhydrine 1 and (-)-β- conhydrine 2 has been achieved by diastereoselective alkylation of an amino aldehyde derivative 7 with ethylmagnesium bromide or diethylzinc.
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 synthesis of (-)-α-conhydrine and its pyrrolidine analogue
Dong, Guang Ri,Hong, Seungmin,Kim, Seung In,Kim, In Su,Jung, Young Hoon
, p. 4200 - 4205 (2012/10/07)
The stereoselective synthesis of (-)-α-conhydrine and its pyrrolidine analogue was achieved from readily available D-erythronolactone. The key step of this synthesis includes a highly regioselective and diastereoselective addition of chlorosulfonyl isocyanate to 1,2-anti-dibenzyl ether to afford the 1,2-anti-amino alcohol. The total synthesis of (-)-α-conhydrine and its pyrrolidine analogue starting from readily available D-erythronolactone was achieved via the regioselective and diastereoselective allylic amination of anti-1,2-dibenzyl ether by using chlorosulfonyl isocyanate.
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.
A straightforward synthesis of conhydrine by hetero Diels-Alder strategy mediated by microwaves
Bandini, Elisa,Corda, Giulia,D'Aurizio, Antonio,Panunzio, Mauro
supporting information; experimental part, p. 933 - 934 (2010/05/18)
Synthesis of optically active conhydrines has been achieved by hetero Diels-Alder cycloaddition assisted by microwaves.
Highly enantioselective synthesis of chiral cyclic amino alcohols and conhydrine by ruthenium-catalyzed asymmetric hydrogenation
Liu, Sheng,Xie, Jian-Hua,Li, Wei,Kong, Wei-Ling,Wang, Li-Xin,Zhou, Qi-Lin
supporting information; experimental part, p. 4994 - 4997 (2009/12/28)
A highly efficient enantio- and diastereoselective synthesis of chiral cis-β-N-alkyl/arylamino cyclic alcohols has been realized by asymmetric hydrogenation of racemic α-amino cyclic ketones via DKR catalyzed by [RuCl2((S)-Xyl-SDP)((R,R)-DPEN)]. The enantioselectivities of the reaction were up to 99.9% ee with 99:1 cis-selectivities. A practical catalytic asymmetric synthesis of all four isomers of conhydrine was also developed.
An approach towards the total synthesis of (+)-epiquinamide and (+)-α-conhydrine from Garner aldehyde
Srivastava, Ajay Kumar,Das, Sanjit Kumar,Panda, Gautam
experimental part, p. 5322 - 5327 (2009/12/01)
A short and stereoselective route for the synthesis of 1-hydroxyquinolizidine, an advanced synthetic intermediate for the total synthesis of (+)-epiquinamide is presented. The key synthetic steps involve diastereoselective nucleophilic addition on l-serin
Metal-dependent reaction tuning with cyclopentylmetal reagents: Application to the asymmetric synthesis of (+)-α-conhydrine and (S)-2-cyclopentyl-2- phenylgrycolic acid
Roy, Siddharth,Sharma, Anubha,Mula, Soumyaditya,Chattopadhyay, Subrata
experimental part, p. 1713 - 1722 (2009/09/07)
The reaction profile of the cyclopentyl organometallic reagents with the aliphatic ketones can be tuned to reduction or addition by changing the metal atom. Cyclopentylmagnesium bromide (CPMB) reduces aromatic and aliphatic aldehydes and ketones to the corresponding alcohols without any C-C bond formation and shows good diastereoselectivity in the reduction of the substituted cyclic and polycyclic ketones as well as chiral α-oxygenated aliphatic ketones. However, in the presence of 10 mol% of ZnClα 2, the cyclopentylmagnesium halides follow a normal Grignard addition to the ketones to give tertiary alcohols with complete diastereoselectivity. The reductive as well as the addition protocols were used for the asymmetric synthesis of two medicinally important compounds, (+)-α-conhydrine and (S)-2-cyclopentyl-2-phenylglycolic acid.
