Synthesis of (+/-)-curcumene ether

被引:0
|
作者
Vickers, TD [1 ]
Keay, BA [1 ]
机构
[1] Univ Calgary, Dept Chem, Calgary, AB T2N 1N4, Canada
关键词
total synthesis; intramolecular Heck reaction; spiro compounds; lactones; natural products;
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 9 step synthesis of (+/-)-curcumene ether is described starting from 5-bromo-2-methyl-2-pentene and 2-amino-5-methylphenol in 7% overall yield using an intramolecular Heck reaction as the key transformation to generate a stereogenic quaternary center.
引用
收藏
页码:1349 / 1351
页数:3
相关论文
共 50 条
  • [21] EFFICIENT AND REGIOSPECIFIC 3-STEP SYNTHESIS OF THE THERMODYNAMICALLY UNFAVORED, NATURALLY OCCURRING, ISOPROPENYL ISOMER OF (+/-)-ALPHA-CURCUMENE - (+/-) ISO-ALPHA-CURCUMENE
    CHAUDHARI, PN
    BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE PARTIE II-CHIMIE MOLECULAIRE ORGANIQUE ET BIOLOGIQUE, 1979, (7-8): : 429 - 430
  • [22] Enantioselective Synthesis of (+)-Nuciferal, (+)-(E)-Nuciferol and (+)-α-Curcumene by Chiral Hydrogenesterification Reaction
    Zhen Ting DU
    Xue Gong SHE
    Guo Ren YUE
    Jun Ying MA
    Yang LI
    Xin Fu PAN State Key Laboratory of Applied Organic Chemistry
    Chinese Chemical Letters, 2004, (12) : 1389 - 1391
  • [23] Enantioselective synthesis of (R)- and (S)-curcumene and curcuphenol:: an efficient chemoenzymatic route
    Kamal, Ahmed
    Malik, M. Shaheer
    Shaik, Ahmad Ali
    Azeeza, Shaik
    TETRAHEDRON-ASYMMETRY, 2007, 18 (21) : 2547 - 2553
  • [24] ASYMMETRIC TOTAL SYNTHESIS OF OPTICALLY-ACTIVE ALPHA-CURCUMENE
    TAMAO, K
    HAYASHI, T
    MATSUMOTO, H
    YAMAMOTO, H
    KUMADA, M
    TETRAHEDRON LETTERS, 1979, (23) : 2155 - 2156
  • [25] SYNTHESIS OF MONOPENOIDS AND SESQUITERPENOIDS .5. DEHYDRO-ALPHA-CURCUMENE
    MORI, K
    AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1972, 36 (03): : 503 - &
  • [26] ISOLATION OF (-)-ALPHA-CURCUMENE, (-)-BETA-CURCUMENE AND (+)-BETA-BISABOLENE FROM GORGONIAN CORALS - ABSOLUTE-CONFIGURATION OF (-) -BETA-CURCUMENE
    JEFFS, PW
    LYTLE, LT
    LLOYDIA-THE JOURNAL OF NATURAL PRODUCTS, 1974, 37 (02): : 315 - 317
  • [27] THE STRUCTURE OF GAMMA-CURCUMENE
    BATT, RD
    SLATER, SN
    JOURNAL OF THE CHEMICAL SOCIETY, 1949, (APR): : 838 - 842
  • [28] Zingiberene and curcumene in wild tomato
    Antonious, GF
    Kochhar, TS
    JOURNAL OF ENVIRONMENTAL SCIENCE AND HEALTH PART B-PESTICIDES FOOD CONTAMINANTS AND AGRICULTURAL WASTES, 2003, 38 (04) : 489 - 500
  • [29] Enantioselective Ir-Catalyzed Hydrogenation of Terminal Homoallyl Sulfones: Total Synthesis of (-)-Curcumene
    Bellido, Marina
    Riego-Mejias, Carlos
    Diaz-Moreno, Alejandro
    Verdaguer, Xavier
    Riera, Antoni
    ORGANIC LETTERS, 2023, 25 (09) : 1453 - 1457
  • [30] CONVENIENT SYNTHESIS OF SESQUITERPENE (+/-)-ALPHA-CURCUMENE .6. APPLICATION OF ALKYLATION-REDUCTION TO TOTAL SYNTHESIS OF TERPENES
    HALL, SS
    MCENROE, FJ
    SHUE, HJ
    JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (22): : 3306 - 3307