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有机化学
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有机化学 ›› 2007, Vol. 27 ›› Issue (12): 1516-1519. 上一篇    下一篇

研究论文

Dihydrokawain和Dihydrokawain-5-ol及其立体异构体的全合成

权伟国a，俞斌勋a，苏瀛鹏a，厍学功*,a,b，潘鑫复*,a   

  1. (a兰州大学化学化工学院 功能有机分子化学国家重点实验室 兰州 730000)
    (b中国科学院兰州化学物理研究所 羰基合成与选择氧化国家重点实验室 兰州 730000)
  • 收稿日期:2007-03-13 修回日期:2007-05-09 发布日期:2007-12-04
  • 通讯作者: 厍学功,潘鑫复

Total Synthesis of All Stereoisomers of Dihydrokawain andDihydrokawain-5-ol

QUAN Wei-Guoa, YU Bin-Xuna, SU Ying-Penga, SHE Xue-Gong*,a,b
PAN Xin-Fu*,a   

  1. (a State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering,
    Lanzhou University, Lanzhou 730000)
    (b State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics,
    Chinese Academy of Sciences, Lanzhou 730000)
  • Received:2007-03-13 Revised:2007-05-09 Published:2007-12-04
  • Contact: SHE Xue-Gong,PAN Xin-Fu

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以苯丙醛和手性丙二烯硼酸酯的加成反应及氧化汞催化下甲醇对羟基丙炔酸的加成反应为关键步骤简短完成了Dihydrokawain和Dihydrokawain-5-ol的所有立体异构体的对映选择性全合成. 以72%的总产率合成了(＋)-Dihy- drokawain, 19%的总产率合成了(＋)-Dihydrokawain-5-ol.

关键词: 全合成, dihydrokawain, dihydrokawain-5-ol, 手性丙二烯硼酸酯

A short total synthesis of all stereoisomers of dihydrokawain and dihydrokawain-5-ol has been achieved. Key steps include a condensation of 3-phenylpropanal with chiral allenylboronic esters and the HgO-catalyzed addition of MeOH to the 5-hydroxy-7-phenylhept-2-ynoic acid. This synthesis afforded (＋)-dihydrokawain in 72% and (＋)-dihydrokawain-5-ol in 19% overall yields respectively.

Key words: dihydrokawain, dihydrokawain-5-ol, chiral allenylboronic ester, total synthesis