Synthetic studies on azadirachtin: Asymmetric synthesis of the tetracyclic decalin part of azadirachtin

被引:0
|
作者
Kanoh, N [1 ]
Ishihara, J [1 ]
Yamamoto, Y [1 ]
Murai, A [1 ]
机构
[1] Hokkaido Univ, Grad Sch Sci, Div Chem, Sapporo, Hokkaido 0600810, Japan
来源
SYNTHESIS-STUTTGART | 2000年 / 13期
关键词
azadirachtin; insect antifeedant; decalin; CBS asymmetric reduction; intramolecular Diels-Alder reaction;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A synthesis of the tetracyclic decalin part of azadirachtin in the naturally occurring form is described. The key reactions involve the Corey-Bakshi-Shibata (CBS) asymmetric reduction of the ketone, and an intramolecular Diels-Alder (IMDA) reaction.
引用
收藏
页码:1878 / 1893
页数:16
相关论文
共 50 条
  • [31] Synthesis of the tricyclic hydroxy acetal of Azadirachtin.
    Wang, XM
    Kraus, GA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 217 : U1221 - U1221
  • [32] Advances of Synthesis and Structure Modification and Bioactivity of Azadirachtin
    Zhang, Huidan
    Zhang, Conghai
    Yan, Shengjiao
    Lin, Jun
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2009, 29 (01) : 20 - 33
  • [33] CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA-INDICA .10. SYNTHESIS OF A HIGHLY FUNCTIONALIZED DECALIN FRAGMENT OF AZADIRACHTIN
    KOLB, HC
    LEY, SV
    TETRAHEDRON LETTERS, 1991, 32 (43) : 6187 - 6190
  • [34] CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA INDICA .4. SYNTHESIS TOWARDS THE LIMONOID AZADIRACHTIN - PREPARATION OF A FUNCTIONALIZED DECALIN FRAGMENT
    LEY, SV
    SOMOVILLA, AA
    BROUGHTON, HB
    CRAIG, D
    SLAWIN, AMZ
    TOOGOOD, PL
    WILLIAMS, DJ
    TETRAHEDRON, 1989, 45 (07) : 2143 - 2164
  • [35] ORGN 121-Toward the total synthesis of azadirachtin
    Boyer, Alistair
    Beckmann, Edith
    Veitch, Gemma E.
    Burke, Brenda J.
    Ley, Steven V.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234
  • [36] Carbohydrate based IMDA/aldol strategy towards the densely functionalized trans-decalin subunit of azadirachtin
    Haag, D
    Chen, XT
    Fraser-Reid, B
    CHEMICAL COMMUNICATIONS, 1998, (23) : 2577 - 2578
  • [37] Development of methods suitable for natural product synthesis: The azadirachtin story
    Ley, SV
    PURE AND APPLIED CHEMISTRY, 2005, 77 (07) : 1115 - 1130
  • [38] Chemistry of insect antifeedants from Azadirachta indica .21. Synthesis of model compounds of azadirachtin using a decalin framework as a functional group scaffolding
    delaPuente, ML
    Ley, SV
    Simmonds, MSJ
    Blaney, WM
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (13): : 1523 - 1529
  • [39] A model synthetic approach towards the furanacetal component of azadirachtin: a potent insect antifeedant
    Raina, S
    Prasad, BAB
    Singh, VK
    ARKIVOC, 2003, : 16 - 24
  • [40] BEHAVIORAL AND NEUROPHYSIOLOGICAL RESPONSES OF SPODOPTERA-LITTORALIS TO AZADIRACHTIN AND A RANGE OF SYNTHETIC ANALOGS
    SIMMONDS, MSJ
    BLANEY, WM
    LEY, SV
    ANDERSON, JC
    BANTELI, R
    DENHOLM, AA
    GREEN, PCW
    GROSSMAN, RB
    GUTTERIDGE, C
    JENNENS, L
    SMITH, SC
    TOOGOOD, PL
    WOOD, A
    ENTOMOLOGIA EXPERIMENTALIS ET APPLICATA, 1995, 77 (01) : 69 - 80