497-88-1Relevant academic research and scientific papers
Decarboxylative Conjunctive Cross-coupling of Vinyl Boronic Esters using Metallaphotoredox Catalysis
Aggarwal, Varinder K.,Duong, Vincent K.,Mega, Riccardo S.,Noble, Adam
supporting information, p. 4375 - 4379 (2020/02/11)
The synthesis of complex alkyl boronic esters through conjunctive cross-coupling of vinyl boronic esters with carboxylic acids and aryl iodides is described. The reaction proceeds under mild metallaphotoredox conditions and involves an unprecedented decarboxylative radical addition/cross-coupling cascade of vinyl boronic esters. Excellent functional-group tolerance is displayed, and application of a range of carboxylic acids, including secondary α-amino acids, and aryl iodides provides efficient access to highly functionalized alkyl boronic esters. The decarboxylative conjunctive cross-coupling was also applied to the synthesis of sedum alkaloids.
Synthesis of (+)-dumetorine and congeners by using flow chemistry technologies
Riva, Elena,Rencurosi, Anna,Gagliardi, Stefania,Passarella, Daniele,Martinelli, Marisa
, p. 6221 - 6226 (2011/06/26)
An efficient total synthesis of the natural alkaloid (+)-dumetorine by using flow technology is described. The process entailed five separate steps starting from the enantiopure (S)-2- (piperidin-2-yl)ethanol 4 with 29 % overall yield. Most of the reactio
A rapid access to (±)-sedamine and some original N -benzyl unsaturated analogues
Boussonniere, Anne,Ranaivondrambola, Tsiresy,Lebreton, Jacques,Mathe-Allainmat, Monique
experimental part, p. 2456 - 2462 (2010/09/04)
Reduction of N-alkyl-2-(2-hydroxy-2-phenylethyl)pyridinium salts using excess of sodium triacetoxyborohydride afforded exclusively the corresponding tetrahydropyridine derivative bearing a piperidine ring with a double bond in the 3,4-position. Furthermore, under these conditions, syn-1,3-amino alcohols were obtained in good yield and diastereoselectivity. 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.
Hydroformylation of homoallylic azides: A rapid approach toward alkaloids
Spangenberg, Thomas,Breit, Bernhard,Mann, Andre
supporting information; experimental part, p. 261 - 264 (2009/08/08)
(Chemical Equation Presented) Unprecedented hydroformylation of homoallylic azides combined with useful one-pot operations provides an expeditive access to alkaloids.
Synthesis of sedamine by cycloisomerisation of an allenic hydroxylamine
Bates, Roderick W.,Nemeth, Joseph A.,Snell, Robert H.
, p. 1033 - 1038 (2008/12/22)
Isoxazolidines have been prepared in a stereoselective manner by treatment of allenic hydroxylamines with silver(I). This methodology has been used in a short synthesis of the alkaloid (+)-sedamine. Georg Thieme Verlag Stuttgart.
Pd-catalyzed enantioselective aerobic oxidation of secondary alcohols: Applications to the total synthesis of alkaloids
Krishnan, Shyam,Bagdanoff, Jeffrey T.,Ebner, David C.,Ramtohul, Yeeman K.,Tambar, Uttam K.,Stoltz, Brian M.
supporting information; experimental part, p. 13745 - 13754 (2009/02/06)
Enantioselective syntheses of the alkaloids (-)-aurantioclavine, (+)-amurensinine, (-)-lobeline, and (-)- and (+)-sedamine are described. The syntheses demonstrate the effectiveness of the Pd-catalyzed asymmetric oxidation of secondary alcohols in diverse contexts and the ability of this methodology to set the absolute configuration of multiple stereocenters in a single operation. The utility of an aryne C-C insertion reaction in accessing complex polycyclic frameworks is also described.
An efficient approach to 2-substituted N-tosylpiperdines: asymmetric synthesis of 2-(2-hydroxy substituted)piperidine alkaloids
Bisai, Alakesh,Singh, Vinod K.
, p. 1907 - 1910 (2007/10/03)
We have developed an efficient and a general approach to chiral 2-substituted N-tosylpiperidines starting from chiral α-substituted-N-tosylaziridines. Using this approach, we have synthesized (+)-coniine. The synthesis of chiral N-tosyl-2-piperidinylethanol 15 and ent-15, was achieved from l- and d-aspartic acids, respectively in few steps. Piperidine 15 was converted into 2-(2-hydroxysubstituted)piperidines of type 2 in optically active form. By applying this strategy, asymmetric syntheses of halosaline (R,R)-2a, (+)- and (-)-sedamine 2b, (+)- and (-)-allosedamine 2c, (+)- and (-)-sedridine 2d, (+)- and (-)-allosedridine 2e, (+)-tetraponerine T-3 3a, T-4 3c, T-7 3b, and T-8 3d have been achieved in high yields. These stereoisomers can be interconverted via Mitsunobu inversion in excellent yields.
Enantioselective synthesis of lobeline via nonenzymatic desymmetrization
Birman, Vladimir B.,Jiang, Hui,Li, Ximin
, p. 3237 - 3240 (2008/02/11)
Lobeline has been prepared in enantiopure form via desymmetrization of lobelanidine with use of BTM, a nonenzymatic enantioselective acyl transfer catalyst.
Stereoselective synthesis of anti-1,3-diol units via Prins cyclisation: application to the synthesis of (-)-sedamine
Yadav,Reddy, M. Sridhar,Rao, P. Purushothama,Prasad
, p. 4397 - 4401 (2007/10/03)
The scope of the Prins cyclisation, the higher stereoselective synthesis of multisubstituted tetrahydropyrans from aldehydes and homoallylic alcohols, is expanded. A new approach for the stereoselective synthesis of polyketide precursors containing anti-1
