高等学校化学学报

高等学校化学学报 ›› 2003, Vol. 24 ›› Issue (10): 1820.

• 论文 • 上一篇    下一篇

螺环倍半萜(±)-α-花柏烯-3-酮的全合成

王进军1, 殷军港1, 邬旭然1, 赵岩1, 竹下齐2, 森章2, 初井敏英2   

  1. 1. 烟台大学应用化学系, 烟台 264005;
    2. 日本九州大学机能物质研究所, 九州
  • 收稿日期:2002-09-19 出版日期:2003-10-24 发布日期:2003-10-24
  • 通讯作者: 王进军(1955年出生),男,博士,教授,从事天然产物和杂环药物的合成研究.E-mail:wjj1955@163.com E-mail:wjj1955@163.com
  • 基金资助:

    国家教委留学回国人员科研启动基金(1998年度)资助

Total Synthesis of (±)-α-Chamigrene-3-one

WANG Jin-Jun1, YIN Jun-Gang1, WU Xu-Ran1, ZHAO Yan1, TAKESHITA Histoshi2, MORI Akira2, HATSUI Toshihide2   

  1. 1. Department of Applied Chemistry, Yantai University, Yantai 264005, China;
    2. Institute of Advanced Material Study, Kyushu University, Kyushu, Japan
  • Received:2002-09-19 Online:2003-10-24 Published:2003-10-24

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摘要： 通过萜品油烯(Terpinolene)与2,4-二氧代戊酸甲酯的deMayo反应得到[2+2]光加成产物,经反aldol重排,再环合成具有螺[5,5]十一烷结构的花柏烯基本碳架,进而对其官能团进行化学修饰,完成了螺环倍半萜(±)-α-花柏烯-3-酮的全合成.

关键词: 螺环化合物, 倍半萜, (±, )-&alpha, -花柏烯, (±, )-&alpha, -花柏烯-3-酮, 全合成

Abstract: In this paper, (±)-α-chamigrene-3-one, a spiro-sesquiterpenoid isolated from Marchantia polymorpha, was synthesized via a useful synthon in the synthesis of chamigrene-type sesquiterpenes, i.e., 1,5,5-trimethyl-1-methoxycarbonylspiroundeca -1,8-dien-3-one(6).This precursor was obtained by the de Mayo reaction of terpinolene with methyl 2,4-dioxopentanoate, followed by the retro-aldol rearrangement of the proto-photocyclo-adducts and then Claisen condensation.The title compound was prepared via compound 6 by further transformed by chemical modification at the functional groups

Key words: Spiro-compound, Sesquiterpenoids, (±)-α-Chamigrene, (±)-α-Chamigrene-3-one, Total synthesis

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