Qinghaosu synthesis

Liu H. J., Chew S. Y., Yeh W. L. Facile Selective Diels-Alder Reactions of Chiral 5,5-Dimethyl-4,6-Methano-2-Methoxycarbonyl-2-Cyclohexenone. Application to the Total Synthesis of Qinghaosu. Youji Huaxue 1993 13 314 321 Keywords (-)-/f-pinene, asymmetric synthesis... 

The exceptional synthesis of qinghaosu (1) is the utilization of the ozonization of vinylsilane to build the peroxy group instead of the photooxidation methods (Scheme... 

Zhou, W.-S. Total synthesis of arteannuin (qinghaosu) and related compounds. Pure Appl. Chem., 1986, 58(5) 817-824. 

Hydroboration-oxidation is a very common method for adding H2O across a double bond. One example is shown in the synthesis of artemisinm (or qinghaosu), the active component of qing-hao, a Chinese herbal remedy used for the treatment of malaria (Figure 10.17). 

Imakura Y, Yokoi T, Yamagishi T, Koyama J, Hu H, McPhail DR, McPhail AT, Lee KH. Synthesis of deethanoqinghaosu, a novel analog of the antimalarial qinghaosu. J. Chem. Soc. Commun. 1988 372. 

Qinghao (Artemisia annua L.) is an important medicinal herb, which has h>een used in the Chinese traditional system of medicine for many centuries. In 1972, Chinese scientists isolated (+)-artemisinin (7, qinghaosu) from the above plant, which is indigenous to China [27-30]. Artemisinin is a sesquiterpene lactone peroxide, whose structure and synthesis have been worked out [27,28]. It has marked activity against both chloroquine-sensitive and resistant strains of Plasmodium falciparum and is particularly suitable for treating cerebral malaria as it is very fast acting [29-31]. 

A short and practical synthesis of qinghaosu and deoxyqinghaosu (102) from arteannuic acid (101) has been developed by Ye and Wu [99] (Scheme 11). 

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