56491-03-3Relevant academic research and scientific papers
STRUCTURE AND TOTAL SYNTHESIS OF DEPLANCHEINE, A NOVEL INDOLOQUINOLIZIDINE ALKALOID
Besselievre, R.,Cosson, J.-P.,Das, B. C.,Husson, H.-P.
, p. 63 - 67 (1980)
The structure of deplancheine 5, an indoloquinolizidine alkaloid of a novel type, has been established from its spectral properties and also by an original synthesis.
An easy ABD→ABCD strategy to indolo[2,3-a]quinolizin-4-one. Synthesis of deplancheine and yohimbane
Chang, Meng-Yang,Chen, Chung-Yi,Chung, Wen-Shang,Tasi, Min-Ruei,Chang, Nein-Chen
, p. 585 - 591 (2007/10/03)
The efficient synthesis of indolo[2,3-a]quinolizin-4-ones 2 is described in two steps via formal [3+3] cycloaddition reaction of α-sulfonyl tryptaminylacetamide 4 with various α,β-unsaturated esters 5 and the regioselective reduction of the resulting glut
Total syntheses of enantiomerically enriched R-(+)- And S-(-)-deplancheinef
Sydorenko, Nadiya,Zificsak, Craig A.,Gerasyuto, Aleksey I.,Hsung, Richard P.
, p. 2140 - 2144 (2007/10/03)
Total syntheses of indoloquinolizidine alkaloid (±)-, R-(+)-, and S-(-)-deplancheine are described here. The synthesis features an enantioselective intramolecular formal aza-[3 + 3] cycloaddition for the construction of the quinolizidine CD-ring. This application serves to introduce a new synthetic strategy for the synthesis of indoloquinolizidine alkaloids. The Royal Society of Chemistry 2005.
Synthesis and conformational study of indolo[2,3-a]-quinolizidine-3-ethan-1'-ols: Intermediates for the synthesis of deplancheine and flavopereirine
Lounasmaa, Mauri,Karinen, Kimmo,Tolvanen, Arto
, p. 1397 - 1404 (2007/10/03)
The synthesis and stereostructures of all four indolo[2,3-a]-quinolizidine-3-ethan-1'-ols are described. The two alcohols with an axial side chain exist principally in the conformation where the C/D ring junction is trans, which is favoured by an intramolecular hydrogen bond between the hydroxyl group and the Nb-atom. Dehydration of the four alcohols with P2O5 in each case led to a mixture consisting of E-deplancheine and Z-deplancheine. The three side products were two 3-vinyl isomers, one of which can be converted to deplancheine via double bond isomerization, and 3-ethyl-1,4,6,7,12,12b-hexahydroindolo[2,3-a]quinolizine, which is a precursor of flavopereirine.
A Short and Effective Synthesis of rac-Deplancheine
Rosenmund, Peter,Hosseini-Merescht, M.
, p. 1321 - 1323 (2007/10/02)
Tryptamine and dimethyl methoxyallylidenemalonate (1) react to give the divinylogous urethane 2, which yields by reaction with acroleine under acid catalysis the β-carboline 3a.Reductive decarboxylation gives the target compound deplancheine (4a) in excellent overall yield. Key Words: Alkaloids / Deplancheine / Indoles / β-Carbolines
SYNTHESIS OF THE ALKALOIDS (+/-)-DEPLANCHEINE AND FLAVOPEREIRINE
Sankar, Parasuraman Jai,Das, Sankar K.,Giri, Venkatachalam S.
, p. 1109 - 1116 (2007/10/02)
Desulfurization of 3-acetyl-1,2,6,7,12,12b-hexahydroindoloquinolizine-2-ethylene thioketal (6) followed by NaBH4 reduction afforded (+/-)-deplancheine (1) whereas NaBH3CN reduction followed by dehydration, desulfurization and DDQ oxidation yielded flavopereirine (2).
Allo-, Epiallo- and Pseudoyohimbanes as well as Heteroyohimbanes by Reaction of a Tetracyclic Aldehyde with Acetoacetate in Different Solvents
Rosenmund, Peter,Casutt, Michael,Wittich, Michael
, p. 233 - 238 (2007/10/02)
The reaction of methyl acetoacetate with 4 in CH3OH/ CH3ONa leads to 11 and 12 with yohimbane skeleton but bicyclo ring E.In DMF/ tBuOK, the epialloheteroyohimbane 13 is produced in fairly good yield, whereas in THF/ NaH the allo-19-hydroxyyohimbinone 17 is formed, which undergoes thermal decomposition to the alloyohimb-18-enone 19.Finally, a full description of an early mentioned synthesis of rac-deplancheine (7) is given.
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
SYNTHESIS OF (+/-)-DEPLANCHEINE
Mandal, Sukhendu B.,Pakrashi, Satyesh C.
, p. 1557 - 1562 (2007/10/02)
The indole alkaloid (+/-)-deplancheine (1) has been synthesized utilizing the intermediate 3-acetyl-1,2,6,7,12,12b-hexahydroindoloquinolizine (6) prepared in two synthetic steps from readily available starting materials.
EINE NEUE TOTALSYNTHESE VON (+/-)DEPLANCHEIN
Rosenmund, Peter,Casutt, Michael
, p. 1771 - 1774 (2007/10/02)
The key step in this synthesis, basing on the toluene-tricarbonylchrome promoted 1.4-H2 addition on the diene 7, proceeds with nearly 100 percent yield and full stereoselectivity.
