Total synthesis of arteannuin (Quinghaosu) and related compounds

Abstract

A new sesquiterpene peroxide was isolated from the chinese her bal medicine Qinghao (Artemisia annua L.). Its structure and absolute stereochemistry have been firmly established by combined spectral, Chemical and X-ray crystallographic methods. Based on pharmacological and chemical studies it was shown to be the antimalarial principle and named arteannuin (qinghaosu). Citronellal was used as a starting material for the total synthesis of arteannuin. The peroxide group of the arteannuin molecule was introduced by photooxidation. Deoxyarteannuin, arteannuin A, arteannuin B, arteannuin E, and arteannuin F which occur together with arteannuin in the same plant were also synthesized. © 1986 IUPAC