Biomimetic synthesis for precursor of muscone

被引:9
|
作者
Shi, Z [1 ]
Qiang, JL [1 ]
Li, Z [1 ]
机构
[1] NW Univ Xian, Dept Chem, Xian 710069, Peoples R China
来源
CHINESE SCIENCE BULLETIN | 2001年 / 46卷 / 05期
关键词
muscone; 2,15-hexadecanedione; biomimetic synthesis;
D O I
10.1007/BF03183272
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
Muscone is a precious fragrant compound scarce in nature. Many attempts have been made to synthesize this unique natural product. In this work, the one-carbon unit transfer reaction of tetrahydrofolate coenzyme was initiated. Benzimidazolium salt was used as the tetrahydrofolate coenzyme model at formic acid oxidation level and di-Grignard reagent as the nucleophile to which one-carbon unit was transferred; the biomimetic synthesis of 2,15-hexade-canedione, a precursor of muscone, was successfully accomplished by using the addition-hydrolysis reaction of benzimidazolium salt with Grignard reagent. And an important useful method for the synthesis of muscone is provided.
引用
收藏
页码:393 / 395
页数:3
相关论文
共 50 条
  • [11] Synthesis of a Biomimetic Tetracyclic Precursor of Aspochalasins and Formal Synthesis of Trichoderone A
    Gayraud, Oscar
    Laroche, Benjamin
    Casaretto, Nicolas
    Nay, Bastien
    ORGANIC LETTERS, 2021, 23 (15) : 5755 - 5760
  • [12] SYNTHESIS OF (R)-MUSCONE
    ABAD, A
    ARNO, M
    PARDO, A
    PEDRO, JR
    SEOANE, E
    CHEMISTRY & INDUSTRY, 1985, (01) : 29 - 30
  • [13] EFFICIENT SYNTHESIS OF (+/-)-MUSCONE
    KORZENIOWSKI, SH
    VANDERBILT, DP
    HENDRY, LB
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1976, 8 (02) : 81 - 84
  • [14] A SYNTHESIS OF ( plus /-)-MUSCONE AND (R)-MUSCONE BY RADICAL RING EXPANSION
    WANG, DS
    WANG, DQ
    ZHOU, CH
    ACTA CHIMICA SINICA, 1995, 53 (09) : 909 - 915
  • [15] Synthesis of (R)- and (S)-muscone
    Fujimoto, S
    Yoshikawa, K
    Itoh, M
    Kitahara, T
    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2002, 66 (06) : 1389 - 1392
  • [16] SYNTHESIS OF (R,S)-MUSCONE
    FLIRI, HG
    SCHOLZ, D
    STUTZ, A
    MONATSHEFTE FUR CHEMIE, 1979, 110 (01): : 245 - 247
  • [17] A practical synthesis of (E)-2-cyclopentadecen-1-one:: an important precursor of macrocyclic muscone
    Hisanaga, Yusuke
    Asumi, Yuya
    Takahashi, Masaki
    Shimizu, Yasuhiro
    Mase, Nobuyuki
    Yoda, Hidemi
    Takabe, Kunihiko
    TETRAHEDRON LETTERS, 2008, 49 (03) : 548 - 551
  • [18] SYNTHESIS OF DL-MUSCONE
    NOKAMI, J
    KUSUMOTO, Y
    JINNAI, K
    KAWADA, M
    CHEMISTRY LETTERS, 1977, (06) : 715 - 716
  • [19] A biomimetic synthesis of a porphobilinogen precursor using a Mukaiyama aldol reaction
    Chaperon, AR
    Engeloch, TM
    Neier, R
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1998, 37 (03) : 358 - 360
  • [20] Biomimetic Synthesis of Twenty-four Long-chained Diketones as Precursors for Muscone and Further Macrocyclic Ketones
    Guo Yuan
    Chen Kang-Yu
    Li Jian-Li
    Shi Zhen
    CHINESE JOURNAL OF CHEMISTRY, 2008, 26 (12) : 2249 - 2255