SYNTHESIS OF A BICYCLIC MODEL FOR THE MARINE HEPATOTOXIN CYLINDROSPERMOPSIN

被引:25
作者
SNIDER, BB
HARVEY, TC
机构
[1] Department of Chemistry Brandeis University, Waltham, MA 02254
基金
美国国家卫生研究院;
关键词
D O I
10.1016/0040-4039(95)00872-A
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A double Michael addition of ammonia to dienone 9 to give piperidinone 10 and the reaction of diamine 16 with isothiocyanate 19 to give protected guanidine 18 are the key transformations in a ten-step synthesis of the cylindrospermopsin model 22.
引用
收藏
页码:4587 / 4590
页数:4
相关论文
共 25 条
  • [1] TOTAL SYNTHESIS OF (+/-)-AGELINE-A, A PHYSIOLOGICALLY ACTIVE CONSTITUENT OF AGELAS SPONGES
    ASAO, K
    IIO, H
    TOKOROYAMA, T
    [J]. TETRAHEDRON LETTERS, 1989, 30 (46) : 6401 - 6404
  • [2] HETEROCYCLIC SYNTHESES WITH ISOTHIOCYANATOFORMIC ESTERS AND THEIR DERIVATIVES
    ATKINS, PR
    GLUE, SEJ
    KAY, IT
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (22): : 2644 - 2646
  • [3] SYNTHESIS OF 1,2-AMINOAZIDES - CONVERSION TO UNSYMMETRICAL VICINAL DIAMINES BY CATALYTIC-HYDROGENATION OR REDUCTIVE ALKYLATION WITH DICHLOROBORANES
    BENALIL, A
    CARBONI, B
    VAULTIER, M
    [J]. TETRAHEDRON, 1991, 47 (38) : 8177 - 8194
  • [4] THE BENZOSTABASE PROTECTING GROUP FOR PRIMARY AMINES - APPLICATION TO ALIPHATIC-AMINES
    BONARLAW, RP
    DAVIS, AP
    DORGAN, BJ
    REETZ, MT
    WEHRSIG, A
    [J]. TETRAHEDRON LETTERS, 1990, 31 (46) : 6725 - 6728
  • [5] A HIGHLY STEREOCONTROLLED, 4-STEP SYNTHESIS OF (+/-)-LASUBINE-II
    BROWN, JD
    FOLEY, MA
    COMINS, DL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (22) : 7445 - 7447
  • [6] SILYLCUPRATION-MEDIATED SYNTHESIS OF 2-SUBSTITUTED ALLYLAMINES
    CAPELLA, L
    DEGL'INNOCENTI, A
    REGINATO, G
    RICCI, A
    TADDEI, M
    SECONI, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (06) : 1473 - 1476
  • [7] MIXED COPPER, ZINC-2-AMINO BENZYLIC ORGANOMETALLICS AS EFFICIENT REAGENTS FOR THE SYNTHESIS OF HETEROCYCLES
    CHEN, HG
    HOECHSTETTER, C
    KNOCHEL, P
    [J]. TETRAHEDRON LETTERS, 1989, 30 (36) : 4795 - 4798
  • [8] Cookston R.C., 1966, TETRAHEDRON S, V22, P355
  • [9] A CONVENIENT PREPARATION OF FARNESYLAMINE
    COPPOLA, GM
    PRASHAD, M
    [J]. SYNTHETIC COMMUNICATIONS, 1993, 23 (04) : 535 - 541
  • [10] USE OF DIMETHYLFORMAMIDE SULFUR-TRIOXIDE COMPLEX AS A SULFATING AGENT OF TYROSINE
    FUTAKI, S
    TAIKE, T
    YAGAMI, T
    OGAWA, T
    AKITA, T
    KITAGAWA, K
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (06): : 1739 - 1744