Attempted synthesis of casbene by intramolecular cyclopropanation

被引：11
|
作者：
Doyle, MP [1 ]
Yan, M [1 ]
机构：
[1] Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
来源：
ARKIVOC | 2002年
关键词：
dirhodium(II) catalysis; vinyldiazomethane; copper(I) catalysis; diterpene; macrocyclization;
D O I：
10.3998/ark.5550190.0003.818
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The antifungal diterpene casbene has been prepared in low yield by intramolecular cyclopropanation of the vinyldiazomethane reactant formed from geranylgeraniol. Careful analysis of the reaction mixture revealed relatively unselective addition catalyzed by dirhodium(II) and copper(I) catalysts.
引用
收藏
页码：180 / 185
页数：6
相关论文
共 50 条
  • [21] FORMATION OF REACTIVE TRICYCLIC INTERMEDIATES VIA THE INTRAMOLECULAR CYCLOPROPANATION OF DIHYDROPYRANS - SYNTHESIS OF EUCALYPTOL
    ADAMS, J
    BELLEY, M
    TETRAHEDRON LETTERS, 1986, 27 (19) : 2075 - 2078
  • [22] Asymmetric intramolecular cyclopropanation. Synthesis of conformationally constrained aminocyclopropane carboxylic acids
    Koskinen, AMP
    Hassila, H
    ACTA CHEMICA SCANDINAVICA, 1996, 50 (04): : 323 - 327
  • [23] New catalyst for intramolecular cyclopropanation reaction
    Yasmin, A
    Jafri, R
    Malik, A
    JOURNAL OF THE CHEMICAL SOCIETY OF PAKISTAN, 2000, 22 (01): : 68 - 70
  • [24] STEREOCHEMISTRY OF INTRAMOLECULAR CYCLOPROPANATION OF AN ORGANOIRON REAGENT
    IYER, RS
    KUO, GH
    HELQUIST, P
    JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26): : 5898 - 5900
  • [25] A superior catalyst for intramolecular cyclopropanation reaction
    Yasmin, A.
    Jafri, R.
    Nelofar, A.
    Ahmed, A.
    JOURNAL OF THE CHEMICAL SOCIETY OF PAKISTAN, 2006, 28 (04): : 361 - 363
  • [26] Intramolecular cyclopropanation of unsaturated terminal aziridines
    Hodgson, DM
    Humphreys, PG
    Ward, JG
    ORGANIC LETTERS, 2006, 8 (05) : 995 - 998
  • [27] Total Synthesis of (-)-Rauvomine B via a Strain-Promoted Intramolecular Cyclopropanation
    Aquilina, Jake M.
    Banerjee, Ankush
    Morais, Gabriel N.
    Chen, Shuming
    Smith, Myles W.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (31) : 22047 - 22055
  • [28] Enantioselective synthesis of fused cycloheptadienes by a tandem intramolecular cyclopropanation/cope rearrangement sequence
    Davies, HML
    Doan, BD
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (23): : 8501 - 8508
  • [29] Intramolecular cyclopropanation of unsaturated terminal epoxides
    Hodgson, DM
    Chung, YK
    Paris, JM
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (28) : 8664 - 8665
  • [30] Intramolecular cyclopropanation of unsaturated terminal epoxides
    Hodgson, David M.
    Chung, Ying Kit
    Paris, Jean-Marc
    1600, American Chemical Society, Columbus, United States (126):
12345