0. A Concise Synthesis of (+)-Artemisinin
CHEM635
Yinzhi Fang
Group C
February 26, 2013
Chunyin Zhu and Silas P. Cook
J. Am. Chem. Soc., 2012, 134 (33), pp 13577–13579

1. Silas P. Cook Education: B.A. Reed College (1999);
Ph.D. Columbia University (2006) Supervisor:Samuel J. Danishefsky;
Postdoctoral Fellow Harvard University ( ) Eric Jacobsen;
In 2009, Silas began his independent appointment in the Chemistry Department at Indiana University, Bloomington.

2. (+)-Artemisinin
also known as Qinghaosu (Chinese: 青蒿素), and its derivatives are a group of drugs that possess the most rapid action of all current drugs against Plasmodium falciparum malaria
The starting compound artemisinin is isolated from the plant Artemisia annua, sweet wormwood, a herb employed in Chinese traditional medicine.
Recent advances in flow chemistry and photochemistry have highlighted an efficient method for the synthesis of artemisinin from its more plentiful biosynthetic precursor artemisinic acid, which is reduced to dihydroartemisinic acid before reacting it with singlet oxygen
—Wiki

3. 3

4. Some Highlights
1.Zinc enolate alkylation
2.Unconventional [4+2] reaction
3.Singlet Oxygen Oxidation

5. Zinc enolate alkylation
Jarugamilli, G. K.; Zhu, C.; Cook, S. P.
Eur. J. Org. Chem. 2012, 1712–1715.

6. Singlet Oxygen Oxidation6

7. Proposed Mechanism 7

8. Conclusion
A cost-effective total synthesis of (+)-artemisinin has been achieved on a gram scale from a widely available, inexpensive starting material, cyclohexenone.