Synthesis of N-[(3S)-2,6-Dioxo-1-(2-phenylethyl)-3-piperidinyl]-(2S)-2-methylbutanamide ((-)-Julocrotine)

被引：9
作者：
Silva, Luciano L. [1 ]
Joussef, Antonio C. [1 ]
机构：
[1] Univ Fed Santa Catarina, Dept Quim, BR-88040900 Florianopolis, SC, Brazil
来源：
JOURNAL OF NATURAL PRODUCTS | 2011年 / 74卷 / 06期
关键词：
GLUTARIMIDE; JULOCROTINE; PROTECTION; ALPHA; ACIDS;
D O I：
10.1021/np200234e
中图分类号：
Q94 [植物学];
学科分类号：
071001 ;
摘要：
The total synthesis of (-)-julocrotine (1) starting from L-glutamic acid in 41% overall yield is described. The methodology utilizes protection, deprotection, and regioselection (carbonyl differentiation via oxazolidinone) protocols, and glutarimide ring formation is the key step.
引用
收藏
页码：1531 / 1534
页数：4
相关论文
共 21 条
  • [1] Julocrotine, a glutarimide alkaloid from Croton membranaceus
    Aboagye, FA
    Sam, GH
    Massiot, G
    Lavaud, C
    [J]. FITOTERAPIA, 2000, 71 (04) : 461 - 462
  • [2] Anastasi C., 1925, AN ASOC QUIM ARGENT, V13, P348
  • [3] PEPTIDE-SYNTHESIS IN AQUEOUS-SOLUTION .4. PREPARATION AND PROPERTIES OF [PARA-(BENZYLOXYCARBONYLOXY)PHENYL]DIMETHYLSULFONIUM METHYL SULFATE (Z-ODSP), [PARA-(TERT-BUTOXYCARBONYLOXY)PHENYL]DIMETHYLSULFONIUM METHYL SULFATE (BOC-ODSP) AND [PARA-(9-FLUORENYLMETHYLOXYCARBONYLOXY)PHENYL]DIMETHYLSULFONIUM METHYL SULFATE (FMOC-ODSP) AS WATER-SOLUBLE NORMAL-ACYLATING REAGENTSL
    AZUSE, I
    TAMURA, M
    KINOMURA, K
    OKAI, H
    KOUGE, K
    HAMATSU, F
    KOIZUMI, T
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (10) : 3103 - 3108
  • [4] REACTION OF ACYLAMINO ACIDS WITH PARAFORMALDEHYDE
    BENISHAI, D
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (21) : 5736 - 5738
  • [5] BLOEMHOFF W, 1975, RECL TRAV CHIM PAY B, V94, P182
  • [6] A short diastereoselective synthesis of 1-aminoindolo-[2,3-a]quinolizidines via an N-acyliminium ion cyclisation
    Ducrot, P
    Thal, C
    [J]. TETRAHEDRON LETTERS, 1999, 40 (51) : 9037 - 9040
  • [7] Design, synthesis, and preliminary pharmacological evaluation of N-acyl-3-aminoglutarimides as broad-spectrum chemokine inhibitors in vitro and anti-inflammatory agents in vivo
    Fox, DJ
    Reckless, J
    Warren, SG
    Grainger, DJ
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (02) : 360 - 370
  • [8] Activity of the julocrotine, a glutarimide alkaloid from Croton pullei var. glabrior, on Leishmania (L.) amazonensis
    Guimaraes, Leda R. C.
    Rodrigues, Ana Paula D.
    Marinho, Patricia S. B.
    Muller, Adolfo H.
    Guilhon, Giselle M. S.
    Santos, Lourivaldo S.
    do Nascimento, Jose Luiz M.
    Silva, Edilene O.
    [J]. PARASITOLOGY RESEARCH, 2010, 107 (05) : 1075 - 1081
  • [9] ITOH M, 1969, CHEM PHARM BULL, V17, P1679
  • [10] 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methyl-morpholinium chloride: An efficient condensing agent leading to the formation of amides and esters
    Kunishima, M
    Kawachi, C
    Morita, J
    Terao, K
    Iwasaki, F
    Tani, S
    [J]. TETRAHEDRON, 1999, 55 (46) : 13159 - 13170
123