164907-52-2Relevant academic research and scientific papers
Total synthesis of (+)-swainsonine and (+)-8-epi-swainsonine
Trajkovic, Milos,Balanac, Vesna,Ferjancic, Zorana,Saicic, Radomir N.
, p. 53722 - 53724 (2014)
Enantioselective synthesis of (+)-swainsonine was achieved in 9 steps, with 24% overall yield. The key feature of the synthesis is the tactical combination of reactions: organocatalyzed aldolization/reductive amination, which allows for a rapid construction of highly functionalized heterocyclic systems. In a similar way (+)-8-epi-swainsonine was synthesized (7 steps, 28%).
Divergent method to trans -5-hydroxy-6-alkynyl/alkenyl-2-piperidinones: Syntheses of (-)-epiquinamide and (+)-swainsonine
Si, Chang-Mei,Mao, Zhuo-Ya,Dong, Han-Qing,Du, Zhen-Ting,Wei, Bang-Guo,Lin, Guo-Qiang
, p. 5824 - 5833 (2015)
An efficient diastereoselective approach to access trans-5-hydroxy-6-alkynyl/alkenyl-2-piperidinones has been developed through nucleophilic addition of α-chiral aldimines using alkynyl/alkenyl Grignard reagents. The diastereoselectivity of alkenyl in C-6
Synthesis of the naringinase inhibitors l-swainsonine and related 6-C-methyl-l-swainsonine analogues: (6R)-C-methyl-l-swainsonine is a more potent inhibitor of l-rhamnosidase by an order of magnitude than l-swainsonine
H?kansson, Anders E.,van Ameijde, Jeroen,Horne, Graeme,Nash, Robert J.,Wormald, Mark R.,Kato, Atsushi,Besra, Gurdyal S.,Gurcha, Sudagar,Fleet, George W.J.
, p. 179 - 184 (2008)
Efficient syntheses are reported of the α-l-rhamnosidase inhibitors l-swainsonine [(1R,2S,8S,8aS)-octahydroindolizine-1,2,8-triol], (6R)-C-methyl-l-swainsonine (1R,2S,6R,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol, (6S)-C-methyl-l-swainsonine (1R,2S,
A divergent approach to 3-piperidinols: A concise syntheses of (+)-swainsonine and access to the 1-substituted quinolizidine skeleton
Archibald, Glenn,Lin, Chih-Pei,Boyd, Peter,Barker, David,Caprio, Vittorio
, p. 7968 - 7980 (2013/01/15)
Nucleophilic addition of Grignard reagents and organolithium species to a 3-silyloxy-3,4,5,6-tetrahydropyridine Noxide provides trans-2,3-disubstituted N-hydroxypiperidines exclusively. The application of this methodology to the preparation of a diversity of useful trans-2-substituted-3-hydroxypiperidines, a concise synthesis of (+)-swainsonine, and an enantiopure 1- substituted quinolizidine of utility in target-directed synthesis is reported.
Radical cyclizations of acylsilanes in the synthesis of (+)-swainsonine and formal synthesis of (-)-epiquinamide
Chen, Ming-Jen,Tsai, Yeun-Min
experimental part, p. 1564 - 1574 (2011/04/15)
Radical cyclization of acylsilane is an useful synthetic methodology. To demonstrate the versatility of this method using the cyclization as a key step, polyhydroxylated indolizidine (+)-swainsonine was synthesized through two different bond connection ap
Asymmetric total synthesis of (+)-swainsonine
Chooprayoon, Soontorn,Kuhakarn, Chutima,Tuchinda, Patoomratana,Reutrakul, Vichai,Pohmakotr, Manat
experimental part, p. 531 - 537 (2011/02/28)
A concise asymmetric synthesis of (+)-swainsonine (ent-1) is described starting from 2, which was readily prepared from commercially available l-glutamic acid. The method features installation of the indolizidine ring via an intramolecular cyclisation of
De novo asymmetric syntheses of d-, l- and 8-epi-d-swainsonine
Guo, Haibing,O'Doherty, George A.
, p. 304 - 313 (2008/04/01)
A highly enantioselective and stereocontrolled approach to d-, l- and 8-epi-d-swainsonine has been developed from achiral furan and γ-butyrolactone. A one-pot hydrogenolysis of both azide and benzyl ether followed by an intramolecular reductive amination has been employed as key step to establish the indolizidine ring system. The absolute stereochemistry was installed by the Noyori reduction and the relative stereochemistry by the use of several highly diastereoselective palladium-catalyzed glycosylation, Luche reduction, dihydroxylation, and palladium-catalyzed azide allylation reactions. This practical approach provide multigram quantities of indolizidine natural product d-swainsonine in 13 steps and 25% overall yield.
Total synthesis of L-(+)-swainsonine and other indolizidine azasugars from D-glucose
Alam, Mohammad Abrar,Kumar, Amit,Vankar, Yashwant D.
experimental part, p. 4972 - 4980 (2009/05/27)
A total synthesis of L-(+)-swainsonine, a potent and specific inhibitor of naringinase, along with the syntheses of six unnatural indolizidine azasugars are reported by starting from D-glucose. L-(+)-Swainsonine was synthesized in 14 steps in 17% overall yield. Further, two of the indolizidine analogues were found to be good glycosidase inhibitors at micromolar concentrations. In all of these syntheses, the key step was an intramolecular SN2 reaction. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
De novo asymmetric synthesis of D- and L-swainsonine
Guo, Haibing,O'Doherty, George A.
, p. 1609 - 1612 (2007/10/03)
The enantioselective syntheses of both enantiomers of the indolizidine natural product swainsonine have been achieved in 13 steps from furan. The indolizidine ring system is installed by a one-pot hydrogenolysis of both an azide and an O-Bn group along with an intramolecular reductive amination reaction. The asymmetry of swainsonine was introduced by Noyori reduction of an acylfuran. This route relies upon an Achmatowicz rearrangement, a diastereoselective palladium-catalyzed glycosylation, Luche reduction, and a dihydroxylation reaction.
