Stereochemical issues related to the synthesis and reactivity of pyrazino[2′,1′-5,1]pyrrolo[2,3-b]indole-1,4-diones

被引:29
作者
Caballero, E [1 ]
Avendaño, C [1 ]
Menéndez, C [1 ]
机构
[1] Univ Complutense, Fac Farm, Dept Quim Organ & Farmaceut, E-28040 Madrid, Spain
关键词
D O I
10.1016/S0957-4166(98)00068-8
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The cyclization of all four diastereoisomers of cyclo-(Trp-Ala) to the corresponding 3,5a,6,10b,11,11a-hexahydro-2H-pyrazino[2',1'-5,1]pyrrolo[2,3-b]indoles is studied from the stereochemical point of view. Epimerization of the tryptophan stereocenter during the cyclization and during acylation reactions of the N-2 atom of the tetracyclic derivatives is discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:967 / 981
页数:15
相关论文
共 28 条
  • [1] ANAND N, 1988, ART ORGANIC SYNTHESI, P330
  • [2] ANTEUNIS MJO, 1978, B SOC CHIM BELG, V87, P627
  • [3] ARAI K, 1989, CHEM PHARM BULL, V37, P2937
  • [4] ASYMMETRIC-SYNTHESIS OF ALPHA-SUBSTITUTED 5-HYDROXY-TRYPTOPHAN DERIVATIVES
    CRICH, D
    LIM, LBL
    [J]. HETEROCYCLES, 1993, 36 (06) : 1199 - 1204
  • [5] NEW DIKETOPIPERAZINE METABOLITES FROM THE SCLEROTIA OF ASPERGILLUS-OCHRACEUS
    DEGUZMAN, FS
    GLOER, JB
    WICKLOW, DT
    DOWD, PF
    [J]. JOURNAL OF NATURAL PRODUCTS, 1992, 55 (07): : 931 - 939
  • [6] NEW METABOLITE, L-ALANYL-L-TRYPTOPHAN ANHYDRIDE FROM ASPERGILLUS-CHEVALIERI
    HAMASAKI, T
    NAGAYAMA, K
    HATSUDA, Y
    [J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1976, 40 (12): : 2487 - 2487
  • [7] Hino T., 1988, ALKALOIDS, V34, P1
  • [8] 5-N-ACETYLARDEEMIN, A NOVEL HETEROCYCLIC COMPOUND WHICH REVERSES MULTIPLE-DRUG RESISTANCE IN TUMOR-CELLS .2. ISOLATION AND ELUCIDATION OF THE STRUCTURE OF 5-N-ACETYLARDEEMIN AND 2 CONGENERS
    HOCHLOWSKI, JE
    MULLALLY, MM
    SPANTON, SG
    WHITTERN, DN
    HILL, P
    MCALPINE, JB
    [J]. JOURNAL OF ANTIBIOTICS, 1993, 46 (03) : 380 - 386
  • [9] VERRUCOFORTINE, A MAJOR METABOLITE OF PENICILLIUM-VERRUCOSUM VAR CYCLOPIUM, THE FUNGUS THAT PRODUCES THE MYCOTOXIN VERRUCOSIDIN
    HODGE, RP
    HARRIS, CM
    HARRIS, TM
    [J]. JOURNAL OF NATURAL PRODUCTS, 1988, 51 (01): : 66 - 73
  • [10] JOHNE S, 1977, PHARMAZIE, V32, P1