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有机化学
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有机化学 ›› 2004, Vol. 24 ›› Issue (10): 1223-1227. 上一篇    下一篇

研究论文

具有岩兰烷基本结构的螺[4,5]癸多烯的合成

王进军*,a, 森章b, 初井敏英b, 竹下b   

  1. a烟台大学应用化学系 烟台 264005;
    b九州大学先导物质化学研究所 福冈 日本
  • 收稿日期:2003-10-08 修回日期:2004-02-27 接受日期:2004-04-19 发布日期:2022-09-20
  • 基金资助:
    国家教委留学回国人员科研启动基金(1998年度)资助项目.

Synthesis of Spiro[4,5]decpolyene with Vetivan-Type Basic Spirocycle Structure

WANG Jin-Jun*,a, MORI Akirab, HATSUI Toshihideb, TAKESHITA Hitoshib   

  1. aDepartment of Applied Chemistry, Yantai University, Yantai 264005;
    bInstitute for Materials Chemical and Engineering, Fukuka, Japan
  • Received:2003-10-08 Revised:2004-02-27 Accepted:2004-04-19 Published:2022-09-20
  • Contact: * E-mail: wjj1955@163.com

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利用1,5-二甲基-6-亚甲基环己烯和2,4-二氧代戊酸甲酯的de Mayo反应,经加成产物retro-benzilic acid 重排,一步构成岩兰烷属螺环倍半萜类天然产物的基本碳架,通过对螺环上的多种官能团进行化学修饰,合成一系列螺[4,5]癸多烯化合物.所合成的新化合物的化学结构均经IR, 1H NMR及元素分析予以证实.

关键词: 光加成, 化学修饰, 岩兰烷结构, 螺环化合物, 合成

In this paper, the basic Vetivan-type framework wasconstructed by photo-addition of methyl 2,4-dioxopentanoate (1) to 1,5-dimethyl-6-methylenecyclohexene (2) and retro-benzilic acid rearrangement of the proto-[2+2]photocycloadduct to afford a spirocyclic compound 3. The chemical modification of function groups on spirocycle was carried out to complete synthesis of a series spiro[4,5]polyenes. The structures of all new compounds were assigned based on the data of IR, 1H NMR and elemental analysis.

Key words: photo-addition, chemical modification, Vetivan-type structure, spirocyclic compound, synthesis