The bromopentadienyl acrylate approach to himbacine

被引:24
作者
Wong, LSM [1 ]
Sharp, LA [1 ]
Xavier, NMC [1 ]
Turner, P [1 ]
Sherburn, MS [1 ]
机构
[1] Univ Sydney, Sch Chem, Sydney, NSW 2006, Australia
关键词
D O I
10.1021/ol0259746
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The syntheses of 4,4a-didehydrohimbacine and 4,4a-didehydrohimandravine are presented. Key steps include an intramolecular Diels-Alder reaction of a bromopentadienyl acrylate and Suzuki-Miyaura and Stille coupling reactions.
引用
收藏
页码:1955 / 1957
页数:3
相关论文
共 31 条
  • [1] THE CARDIOSELECTIVITY OF HIMBACINE - A MUSCARINE RECEPTOR ANTAGONIST
    ANWARUL, S
    GILANI, H
    COBBIN, LB
    [J]. NAUNYN-SCHMIEDEBERGS ARCHIVES OF PHARMACOLOGY, 1986, 332 (01) : 16 - 20
  • [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] ALPHA-LITHIOAMINE SYNTHETIC EQUIVALENTS - SYNTHESES OF DIASTEREOISOMERS FROM BOC DERIVATIVES OF CYCLIC AMINES
    BEAK, P
    LEE, WK
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) : 1109 - 1117
  • [4] Palladium-catalysed hydrostannylations of 1-bromoalkynes. A practical synthesis of (E)-1-stannylalk-1-enes
    Boden, CDJ
    Pattenden, G
    Ye, T
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (20): : 2417 - 2419
  • [5] PREPARATION OF ETHEREAL SOLUTIONS OF 1-LITHIOCYCLOHEXENE AND 1-LITHIOCYCLOHEPTENE FROM THE CHLOROCYCLOALKENES AND LITHIUM
    BRANDSMA, L
    VERKRUIJSSE, HD
    [J]. SYNTHETIC COMMUNICATIONS, 1990, 20 (21) : 3367 - 3369
  • [6] CAUWENBERGE GV, 2002, ORG LETT, V4, P1579
  • [7] Cayzer TN, 2002, CHEM-EUR J, V8, P739, DOI 10.1002/1521-3765(20020201)8:3<739::AID-CHEM739>3.0.CO
  • [8] 2-1
  • [9] Total synthesis of himandravine
    Chackalamannil, S
    Davies, R
    McPhail, AT
    [J]. ORGANIC LETTERS, 2001, 3 (10) : 1427 - 1429
  • [10] 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