Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (3): 578-583.DOI: 10.6023/cjoc201309023 Previous Articles     Next Articles

Articles

基于光诱导单电子转移反应的三环异吲哚酮并环肽的合成

董超, 谭广慧, 金英学   

  1. 哈尔滨师范大学化学化工学院化学系 哈尔滨 150025
  • 收稿日期:2013-09-16 修回日期:2013-10-11 发布日期:2013-11-05
  • 通讯作者: 金英学 E-mail:yenghak@hrbnu.edu.cn;tgh.123@163.com
  • 基金资助:

    国家自然科学基金(Nos. 20972036,21272048);黑龙江省自然科学基金(No. B20913);黑龙江省高效科技创新团队建设计划(No. 2011TD010)资助项目.

Synthesis of Tricyclic Isoindole Cyclic Peptide Based on Photoinduced Single Electron Trasfer Reaction

Dong Chao, Tan Guanghui, Jin Yingxue   

  1. College of Chemistry &Chemical Engineering, Harbin Normal University, Harbin 150025
  • Received:2013-09-16 Revised:2013-10-11 Published:2013-11-05
  • Supported by:

    Project supported by the National Natural Sciences Foundation of China (Nos. 20972036, 21272048), the Natural Sciences Foundatjion of Heilongjiang Province (No. B20913) and the Program for Scientific Technological Innovation Team Construction in Universites of Heilongjiang Province (No. 211TD010).

Exploratory photochemical studies on phthalimido-polypeptides 1a1h in which phthalimides worked as light absorbance acceptors and polypeptide served as electron donor centers have been conducted, leading to the development of synthetic methodology to construct tricyclic isoindole cyclopeptide mimetics. It was found that irradiation on 1a, 1b, 1d1h in methanol led to efficient generation of tricyclic isoindole cyclic peptides 2a, 2b, 2d2h, which may be through sequential single electron transfer (SET) pathway. The structures of new compounds were determined by NMR and HRMS spectroscopy.

Key words: photoreaction, single electron transfer (SET), cyclic peptide, phthalimide, tricyclic isoindole cyclic peptide