A novel short convergent entry into himbacine derivatives

被引:12
作者
Van Cauwenberge, G
Gao, LJ
Van Haver, D
Milanesio, M
Viterbo, D
De Clercq, PJ
机构
[1] State Univ Ghent, Dept Organ Chem, B-9000 Ghent, Belgium
[2] Univ Piemonte Orientale A Avogadro, Dipartimento Sci & Tecnol Avanzate, I-15100 Alessandria, Italy
关键词
D O I
10.1021/ol025801g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The IMDA reaction of 9 leads with good stereoselectivity to exo-adduct 10b. The functionalized ABC-ring core in 10 is well suited for the convergent synthesis of analogues of himbacine, a naturally occurring M-2 selective muscarine receptor antagonist, as illustrated with the further synthesis of the dehydro-derivative 5.
引用
收藏
页码:1579 / 1582
页数:4
相关论文
共 38 条
  • [1] [Anonymous], 1991, Comprehensive Organic Synthesis
  • [2] Studies towards a postulated biomimetic Diels-Alder reaction for the synthesis of himgravine
    Baldwin, JE
    Chesworth, R
    Parker, JS
    Russell, AT
    [J]. TETRAHEDRON LETTERS, 1995, 36 (52) : 9551 - 9554
  • [3] BROWN RFC, 1956, AUST J CHEM, V9, P283
  • [4] CAPELLA L, 1991, SYNTHESIS-STUTTGART, P1201
  • [5] Total synthesis of himandravine
    Chackalamannil, S
    Davies, R
    McPhail, AT
    [J]. ORGANIC LETTERS, 2001, 3 (10) : 1427 - 1429
  • [6] Total synthesis of (+)-himbacine and (+)-himbeline
    Chackalamannil, S
    Davies, RJ
    Wang, Y
    Asberom, T
    Doller, D
    Wong, J
    Leone, D
    McPhail, AT
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (06) : 1932 - 1940
  • [7] A highly efficient total synthesis of (+)-himbacine
    Chackalamannil, S
    Davies, RJ
    Asberom, T
    Doller, D
    Leone, D
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (40) : 9812 - 9813
  • [8] Ciganek E., 1984, ORG REACT NY, V32, P1, DOI DOI 10.1002/0471264180.OR032.01
  • [9] ALZHEIMERS-DISEASE - A DISORDER OF CORTICAL CHOLINERGIC INNERVATION
    COYLE, JT
    PRICE, DL
    DELONG, MR
    [J]. SCIENCE, 1983, 219 (4589) : 1184 - 1190
  • [10] STEREOCHEMICAL ASPECTS OF THE INTRAMOLECULAR DIELS-ALDER REACTION
    CRAIG, D
    [J]. CHEMICAL SOCIETY REVIEWS, 1987, 16 (02) : 187 - 238