76549-66-1Relevant academic research and scientific papers
IMINE-ENAMINE ANNELATION: STEREOSELECTIVE SYNTHESES OF (+/-)-DEPLANCHEINE
Calabi, Luisella,Danieli, Bruno,Lesma, Giordano,Palmisano, Giovanni
, p. 2139 - 2142 (1982)
Two new approaches to synthesis of (+/-)-deplancheine (1) are described which utilize the alkylation of the imine-enamine (2) as the key ring-forming step.
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.
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.
Stereocontrolled Synthesis of Exocyclic Trisubstituted Double Bonds by Stereospecific Iminium Ion-Vinylsilane Cyclizations. A Short Synthetic Route to Indoloquinolizidine Alkaloids
Overman, Larry E.,Malone, Thomas C.
, p. 5297 - 5300 (2007/10/02)
The reaction of (Z)- and (E)-trisubstituted vinylsilanes 9 and 10 with paraformaldehyde and acid proceeded with >98percent retention of configuration to give indoloquinolizidines 13 and 3 in excellent yield.This is the first demonstration that iminium ion-vinylsilane cyclizations occur with complete retention of configuration with either vinylsilane stereoisomer.The simple indole alkaloid dl-deplancheine (3) was prepared in a stereocontrolled fashion in 26percent overall yield from commercially available 1-(trimethylsilyl)propyne.
A total synthesis of the alkaloid deplancheine
Ashcroft,Joule
, p. 2341 - 2344 (2007/10/02)
The indole alkaloid deplancheine (1) has been synthesised utilising a Witting reaction on the octahydro[2,3-a]quinolizin-2-one (2) itself available in four synthetic steps from readily available materials.
