Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (7): 2820-2830.DOI: 10.6023/cjoc202102021 Previous Articles     Next Articles


基于分子内的仿生Diels-Alder反应构建Elansolid A1/A2的四氢茚烷核心结构

于奇a, 杨帅b, 唐聪云a, 彭林a,*(), 左之利b,*(), 汪亮亮b,*()   

  1. a 邵阳学院食品与化学工程学院 湖南邵阳 422000
    b 中国科学院昆明植物研究所 昆明 650201
  • 收稿日期:2021-02-06 修回日期:2021-03-30 发布日期:2021-04-06
  • 通讯作者: 彭林, 左之利, 汪亮亮
  • 基金资助:
    中国科学院“西部之光”; 中国科学院青年创新促进会; 国家自然科学基金(21772207); 云南省千人计划; 湖南省教育厅(19c1655)

Biomimetic Intramolecular Diels-Alder Reaction to Construct the Tetrahydroindane Core of Elansolid A1/A2

Qi Yua, Shuai Yangb, Congyun Tanga, Lin Penga(), Zhili Zuob(), Liangliang Wangb()   

  1. a School of Food and Chemical Engineering, Shaoyang University, Shaoyang, Hunan 422000
    b State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201
  • Received:2021-02-06 Revised:2021-03-30 Published:2021-04-06
  • Contact: Lin Peng, Zhili Zuo, Liangliang Wang
  • Supported by:
    “Light of West China” Program; Youth Innovation Promotion Association of the Chinese Academy of Sciences; National Natural Science Foundation of China(21772207); “Thousand Talents Program” of Yunnan Province; Program from Education Department of Hunan Province(19c1655)

The Elansolid A1/A2 is metabolite from the gliding bacteriumChitinophaga sanctiiand shows antibiotic activity against Gram-positive bacteria. Up to now, the total synthesis of this natural product has not been reported yet due to its structure complexity, which arises from thetrans-tetrahydroindane unit and (Z)-(E)-(Z) triene motif as well as a 19-member macrolactone. In this study, two newO-functionalized substrates were synthesized to undergo the biomimetic intramolecular Diels-Alder reactions (IMDA) catalyzed by a chiral phosphoric acid to build the keytrans-tetrahydroindane core of Elansolid A1/A2 via a vinylicp-quinone methide intermediate. This result shows that an improveddr (1.8∶1) of IMDA reaction and shorter synthetic steps could be achieved.

Key words: biomimetic synthesis, Diels-Alder reaction, tetrahydroindane, elansolid