Acta Chimica Sinica ›› 1982, Vol. 40 ›› Issue (11): 1081-1083. Previous Articles     Next Articles

青蒿素类似物的立体专一性合成

许杏祥, 黄大中, 朱杰, 周维善   

  1. 中国科学院上海有机化学研究所
  • 投稿日期:1982-04-01 发布日期:2013-06-03
  • 通讯作者: 许杏祥

THE STEREO-CONTROLLED SYNTHESIS OF ARTEANNUIN ANALOG

XU XING-XIANG, HUANG DA-ZHONG, ZHU JIE, ZHOU WEI-SHAN   

  1. Shanghai Institute of Organic Chemistry, Academia Sinica
  • Received:1982-04-01 Published:2013-06-03

Arteannuin (1) was a new sesduiterpenoid containing a, peroxide linkage and ie the antimalarial principle isolated from Artemisia amnua L.The present investigation deals with the synthesis of its analog 8, which contained tho peroxide moiety in the molecule, starting from arteannuinic acid (2) through photo-oxidation. The key intermediate 5 was obtained from 2 via esterifioation, selective NaBH4 reduction and alkaline hydrolysis. Irradiation of a dilute pyridine elution of 6 in the presence of oxygen and a sensitizer (hematoporphyrin) with 200W high pressure mercury lamp gave the a-hydroperoxide 6. Ozonolysis of 6 in diohloromethane-pyridine afforded the aoetal 7. Activation of the carboxyl group in 7 with TsCl-Et3N resulted in the cyolization of the lactone ring, to afford the final product, arteannuin analog 8.