32283-51-5Relevant academic research and scientific papers
2,5-dimethoxy-2,5-dihydrofuran as a synthetic equivalent of 3-formyl alkylpropionate in pictet-spengler type reactions
Fontaine, Helene,Baussanne, Isabelle,Royer, Jacques
, p. 2817 - 2824 (1997)
2,5-dimethoxy-2,5-dihydrofuran has been used as a synthetic equivalent of 3-formyl propionate in the Pictet-Spengler type reaction of 2-aryl ethylamines to provide the corresponding arylindolizidinones in moderate yields.
Asymmetric Synthesis of (R)-1-Alkyl-Substituted Tetrahydro-?-carbolines Catalyzed by Strictosidine Synthases
Pressnitz, Desiree,Fischereder, Eva-Maria,Pletz, Jakob,Kofler, Christina,Hammerer, Lucas,Hiebler, Katharina,Lechner, Horst,Richter, Nina,Eger, Elisabeth,Kroutil, Wolfgang
supporting information, p. 10683 - 10687 (2018/08/17)
Stereoselective methods for the synthesis of tetrahydro-?-carbolines are of significant interest due to the broad spectrum of biological activity of the target molecules. In the plant kingdom, strictosidine synthases catalyze the C?C coupling through a Pictet–Spengler reaction of tryptamine and secologanin to exclusively form the (S)-configured tetrahydro-?-carboline (S)-strictosidine. Investigating the biocatalytic Pictet–Spengler reaction of tryptamine with small-molecular-weight aliphatic aldehydes revealed that the strictosidine synthases give unexpectedly access to the (R)-configured product. Developing an efficient expression method for the enzyme allowed the preparative transformation of various aldehydes, giving the products with up to >98 % ee. With this tool in hand, a chemoenzymatic two-step synthesis of (R)-harmicine was achieved, giving (R)-harmicine in 67 % overall yield in optically pure form.
Syntheses of fused tetrahydro-β-carboline analogues through imide carbonyl activation using BBr3: Evidence for the involvement of fused cyclic N-acyliminium ion intermediate
Mangalaraj, Selvaraj,Selvakumar, Jayaraman,Ramanathan, Chinnasamy Ramaraj
, p. 811 - 819 (2015/08/06)
Abstract The fused cyclic N-acyliminium ion generated during the imide carbonyl activation reaction of phenethylphthalimide was confirmed by single crystal X-ray diffraction. The Lewis acid assisted imide carbonyl activation methodology was successfully extended to synthesize fused tetrahydro-β-carboline units from the corresponding N-indolylethylimides. [Figure not available: see fulltext.]
Application of chlorotrimethylsilane in Pictet-Spengler reaction
Ryabukhin, Sergey V.,Panov, Dmitriy M.,Plaskon, Andrey S.,Tolmachev, Andrey A.,Smaliy, Radomyr V.
, p. 1507 - 1517 (2013/02/21)
Chlorotrimethylsilane has been found to be an efficient condensing agent in the Pictet-Spengler reaction, affording an extremely straightforward synthetic route to tetrahydro-β-carboline derivatives and their analogs. The applicability of the method has b
Synthesis of heterocycles through a ruthenium-catalyzed tandem ring-closing metathesis/isomerization/N-acyliminium cyclization sequence
Ascic, Erhad,Jensen, Jakob F.,Nielsen, Thomas E.
, p. 5188 - 5191 (2011/06/26)
Tandem bicycle: In the title reaction double bonds created during ring-closing metathesis isomerize to generate reactive iminium intermediates that undergo intramolecular cyclization reactions with tethered heteroatom and carbon nucleophiles. In this way, a series of biologically interesting heterocyclic compounds can be made, including a known precursor for the total synthesis of the antiparasitic natural product harmicine. Copyright
Facile synthesis of 2,3,6,11-tetrahydro-1H,5H-indolizino[8,7-b]indole-11b- carboxylic acid methyl ester via a 9-BBN-mediated tertiary lactam reduction
Fokas, Demosthenes,Wang, Zhimin
, p. 3816 - 3822 (2008/12/23)
A facile synthesis of 2,3,6,11-tetrahydro-1H,5H-indolizino[8,7-b]indole- 11b-carboxylic acid methyl ester, a versatile intermediate utilized in the synthesis of indole alkaloids, was achieved in two steps. Condensation of tryptamine with dimethyl α-ketoglutarate led to the formation of the corresponding indolizino[8,7-b]indolone ester, which subsequently underwent an efficient lactam reduction with 9-BBN to generate the tertiary amine ester in good yield. Copyright Taylor & Francis Group, LLC.
Carboxyl-Mediated Pictet-Spengler Reaction. Direct Synthesis of 1,2,3,4-Tetrahydro-β-carbolines from Tryptamine-2-carboxylic Acids
Narayanan, Krishnaswamy,Schindler, Liesl,Cook, James M.
, p. 359 - 365 (2007/10/02)
The Pictet-Spengler condensation of various tryptamine-2-carboxylic acids 9a-f with carbonyl compounds in benzene/dioxane/trifluoroacetic acid (Table I) with simultaneous loss of carbon dioxide afforded directly the corresponding 1,2,3,4-tetrahydro-β-carb
Carboxyl-mediated Pictet-Spengler reaction. Direct synthesis of 1,2,3,4-tetrahydro β-carbolines from tryptamine-2-carboxylic acids
Narayanan, Krishnaswamy,Cook, James M.
, p. 3397 - 3400 (2007/10/02)
The Pictet-Spengler condensation of various tryptamine-2-carboxylic acids 1 with carbonyl compounds in benzene/dioxane/trifiuoroacetic acid (Table) with simultaneous loss of carbon dioxide, afforded directly the corresponding 1,2,3,4-tetrahydro β-carbolin
Reduction of Lactams and Thiolactams by Sodium Borohydride: Application in the Synthesis of Some Alkaloids
Mandal, S. B.,Giri, V. S.,Sabeena, M. S.,Pakrashi, S. C.
, p. 4236 - 4241 (2007/10/02)
Lactams 1a-8a and thiolactams 1b-8b,9a,10b-12b and 13 could be reduced to their corresponding amines in 70-98percent yield by using borohydide-tert-butyl alcohol-methanol mixtures under reflux.Even the vinylogous amide 19 underwent reduction to afford dep
A New Synthesis of β-Carbolines
Atta-ur-Rahman,Sultana, Mumtaz
, p. 535 - 536 (2007/10/02)
A new one step synthesis of β-carbolines is described, which involves the direct conversion of N-imidotryptamines to the corresponding lactams on reaction with P2S5. - Keywords: β-Carbolines, Indole Alkaloids
