Tetrahedron

Synthesis of an immunomodulator (+)-conagenin and its analogs

T Yakura, Y Yoshimoto, C Ishida, S Mabuchi

Index: Yakura, Takayuki; Yoshimoto, Yuya; Ishida, Chisaki; Mabuchi, Shunsuke Tetrahedron, 2007 , vol. 63, # 21 p. 4429 - 4438

Full Text: HTML

Citation Number: 35

Abstract

Stereoselective synthesis of an immunomodulator (+)-conagenin was achieved. Both amine and carboxylic acid moieties were prepared from commercially available optically active methyl 3-hydroxy-2-methylpropanoate using dirhodium (II)-catalyzed C–H amination and chelation-controlled reductions as key steps. In addition, demethyl analogs of conagenin were synthesized using similar procedures.

Related Articles:

Synthesis, radiolabeling, and biological evaluation of (R)-and (S)-2-amino-3-[18F] fluoro-2-methylpropanoic acid (FAMP) and (R)-and (S)-3-[18F] fluoro-2-methyl-2-N-( …

[Yu, Weiping; McConathy, Jonathan; Olson, Jeffrey; Camp, Vernon M.; Goodman, Mark M. Journal of Medicinal Chemistry, 2007 , vol. 50, # 26 p. 6718 - 6721]

α-substituted quisqualic acid analogs: New metabotropic glutamate receptor group II selective antagonists

[Kozikowski, Alan P.; Steensma, Darryl; Varasi, Mario; Pshenichkin, Sergey; Surina, Elena; Wroblewski, Jarda T. Bioorganic and Medicinal Chemistry Letters, 1998 , vol. 8, # 5 p. 447 - 452]

Enantioselective synthesis of (S)-and (R)-α-methylserines: application to the synthesis of (S)-and (R)-N-Boc-N, O-isopropylidene-α-methylserinals

[Avenoza, Alberto; Cativiela, Carlos; Corzana, Francisco; Peregrina, Jesus M.; Sucunza, David; Zurbano, Maria M. Tetrahedron Asymmetry, 2001 , vol. 12, # 6 p. 949 - 957]

Enantioselective synthesis of (S)-and (R)-α-methylserines: application to the synthesis of (S)-and (R)-N-Boc-N, O-isopropylidene-α-methylserinals

[Avenoza, Alberto; Cativiela, Carlos; Corzana, Francisco; Peregrina, Jesus M.; Sucunza, David; Zurbano, Maria M. Tetrahedron Asymmetry, 2001 , vol. 12, # 6 p. 949 - 957]

Et2AlCl-Catalyzed Cyclization of Epoxytrichloroacetimidates for the Synthesis of α-Substituted Serines

[Hatakeyama; Matsumoto; Fukuyama; Mukugi; Irie Journal of Organic Chemistry, 1997 , vol. 62, # 7 p. 2275 - 2279]

More Articles...