60900-14-3Relevant academic research and scientific papers
Synthesis of new azocine derivatives and their functionalization by nucleophilic addition to their iminium salts
Badaro Trindade, Angela Cristina Leal,Dos Santos, Daniela Cristina,Gil, Laurent,Marazano, Christian,Pereira De Freitas Gil, Rossimiriam
, p. 1052 - 1057 (2007/10/03)
A route to the eight-membered nitrogen heterocycles 20a,b is described starting from the 3-alkyl-N-benzylpyridinium salts 14a,b. These azocine derivatives were converted into their respective iminium salts 11 by treatment with methanesulfonic acid. A stud
Synthesis of 2,3-disubstituted indoles by radical cyclization with hypophosphorous acid and its application to total synthesis of (±)-catharanthine
Reding, Matthew T.,Kaburagi, Yosuke,Tokuyama, Hidetoshi,Fukuyama, Tohru
, p. 313 - 330 (2007/10/03)
Radical cyclization of o-alkenylthioanilides using hypophosphorous acid and AIBN in the presence of Et3N proceeded smoothly to furnish the corresponding 2,3-disubstituted indoles in high yields. Utilizing the newly developed cyciization condition, a stereocontrolled total synthesis of (±)-catharanthine has been completed.
Stereocontrolled total synthesis of (±)-catharanthine via radical-mediated indole formation
Reding, Matthew T.,Fukuyama, Tohru
, p. 973 - 976 (2008/02/09)
(matrix presented) A stereocontrolled total synthesis of (±)-catharanthine, 1, has been completed. The key step involves the radical-mediated cyclization of a highly functionalized intermediate to furnish the corresponding indole. The cyclization utilizes
On the preparation of amine N-oxides by using dioxiranes
Ferrer, Marta,Sanchez-Baeza, Francisco,Messeguer, Angel
, p. 15877 - 15888 (2007/10/03)
The reaction of heterocyclic aromatic amines, anilines and tertiary amines with dimethyldioxirane (DMD) was examined. Treatment of heterocyclic aromatic amines and anilines with a slight excess of DMD at 0°C afforded the corresponding N-oxides in quantitative conversion yields. In addition, the oxidation was chemoselective in the presence of carbon-carbon double bonds. On the other hand, most of the tertiary amines assayed did afford also quantitative yields of the corresponding N. oxides, although reaction conditions, in particular regarding the amount of DMD required, depended on each substrate. Additional studies carried out on selected substrates suggested that certain N-oxides derived from tertiary amines deactivate DMD.
SYNTHESIS OF VINCA ALKALOIDS AND RELATED COMPOUNDS XLVIII SYNTHESIS OF (+)-CATHARANTHINE AND (+/-)-ALLOCATHARANTHINE
Szantay, Csaba,Boelcskei, Hedvig,Gacs-Baitz, Eszter
, p. 1711 - 1732 (2007/10/02)
The first synthesis of natural (+)-catharanthine (1) has been achieved in a few steps and in ca. 20 percent overall yield based on indole-3-acetic acid.The isomeric (+/-)-allocatharanthine was also prepared.
Synthesis of (+/-)-Catharanthine, (+)-Anhydrovinblastine, and (-)-Anhydrovincovaline
Raucher, Stanley,Bray, Brian L.,Lawrence, Ross F.
, p. 442 - 446 (2007/10/02)
An efficient total synthesis of (+/-)-catharanthine (1) has been accomplished.Diels-Alder reaction of 8 with α-chloroacryloyl chloride followed by reaction with MeOH gave 9.Treatment of 9 with Me3SiI gave 10, and reaction of 10 with indole-3-acetyl chloride provided 11, which was converted to 13.Irradiation of 13 in CH3CN/H2O with a 450-W Hanovia mercury lamp through a Pyrex filter provided 14.Reduction of 14 by treatment with Et3OBF4 and NaBH3CN gave (+/-)-catharanthine (1).The coupling of synthetic (+/-)-catharanthine with natural (-)-vindoline (2) via modified Polonovski reaction provided (+)-anhydrovinblastine (15a) and (-)-anhydrvincovaline (17a), which could be easily separated by flash chromatography.
2-Cyano-Δ3-piperideines. 12. Stereochemistry of Formation of N-Benzyl-2-cyano-Δ3-piperideines and Facile Isomerization on Alumina to 2-Cyano-Δ4-piperideines. A Potentially General Route to the Synthesis of 2,6-Disubstitute
Bonin, Martine,Romero, Jose Ricardo,Grierson, David S.,Husson, Henri-Philippe
, p. 2392 - 2400 (2007/10/02)
The reaction of the piperideine N-oxides 1a-f with trifluoroacetic anhydride in CH2Cl2 at 0 deg C (Polonovski-Potier reaction) led to the formation of the N-benzyl-2-cyano-Δ3-piperideines 3a-f.Epimeric mixtures were obtained for the amino nitri
PREPARATION AND DIELS-ALDER REACTION OF N-CARBOMETHOXY-5-ETHYL-1,2-DIHYDROPYRIDINE: AN APPROACH FOR THE SYNTHESIS OF CATHARANTHINE
Raucher, Stanley,Lawrence, Ross F.
, p. 2927 - 2930 (2007/10/02)
N-carbomethoxy-5-ethyl-1,2-dihydropyridine (1) may be prepared by the bromination of N-carbomethoxy-3-ethyl-1,2,5,6-tetrahydropyridine (10), and subsequvent double dehydrobromination with EtAlCl2/HMPA; this diene undergoes Diels-Alder reaction with dimethyl methylenemalonate (2) to give the isoquinuclidine (3), an intermediate in our planned approach to catharanthine.
INTRAMOLECULAR HYDRIDE TRANSFER AND CYCLIZATION OF 5-OXO-Na-TOSYL-14,21-DEHYDROSECODINE
Raucher, Stanley,Lawrence, Ross F.
, p. 3731 - 3736 (2007/10/02)
5-Oxo-Na-tosyl-14,21-dehydrosecodine (8) was prepared by bromination of 6 followed by double dehydrobromination with ethyl aluminum dichloride in HMPA.When a dilute solution of 8 was heated, 10 was formed via intramolecular hydride transfer and cyclization.
