高等学校化学学报

高等学校化学学报 ›› 1998, Vol. 19 ›› Issue (S1): 139.

• Organic Synthesis Chemistry • 上一篇    下一篇

The First Efficient Approach from α-(-)-Santonin to Dihydroagarofuran Sesquiterpene

Biangdong Sun, Yongqiang Tu, Wujiong Xia, Bin Wu   

  1. Chemistry Department, the National Laboratory of Applied Organic Chemistry, Lanzhou University 730000, Lanzhou
  • 出版日期:1998-12-31 发布日期:1998-12-31
  • 基金资助:
    Financial support from the National Foundation of Natural Science of China

The First Efficient Approach from α-(-)-Santonin to Dihydroagarofuran Sesquiterpene

Biangdong Sun, Yongqiang Tu, Wujiong Xia, Bin Wu   

  1. Chemistry Department, the National Laboratory of Applied Organic Chemistry, Lanzhou University 730000, Lanzhou
  • Online:1998-12-31 Published:1998-12-31
  • Supported by:
    Financial support from the National Foundation of Natural Science of China

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摘要： The naturally occurring dihydroagarofuran compounds have been demonstrated to show some important bioactive activities, such as insect antifeedant, antitumor activities.1 Synthetic research of this kind of compounds have been attracting the increasing interest of organic chemists. Because a total synthesis of polyol skeleton involved too many steps,2 our synthetic efforts are focusing on search for a short and efficient approach and thus, we begin with readily available α-(-)-santonin(1). The creative key steps include generation of C5-OH, the stereochemical reversion at C-7 and the cyclization of tetrahydrofuran. A successful approach is shown in the following scheme.

Abstract: The naturally occurring dihydroagarofuran compounds have been demonstrated to show some important bioactive activities, such as insect antifeedant, antitumor activities.1 Synthetic research of this kind of compounds have been attracting the increasing interest of organic chemists. Because a total synthesis of polyol skeleton involved too many steps,2 our synthetic efforts are focusing on search for a short and efficient approach and thus, we begin with readily available α-(-)-santonin(1). The creative key steps include generation of C5-OH, the stereochemical reversion at C-7 and the cyclization of tetrahydrofuran. A successful approach is shown in the following scheme.

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