Total synthesis of (-)-qinghaosu IV (artemisinin D, arteannuin D)

Heterocycles

Volumn 42, Issue 2, 1996, Pages 493-497

  Liu, Hsing Jang ^a   Yeh, Wen Lung ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0345014971     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-95-S74     Document Type: Article

References (15)

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2. For a recent review, see W. S. Zhou and X. X. Xu, Acc. Chem. Res., 1994, 27, 211.
3. I. S. Lee, H. N. ElSohly, E. M. Croom, and C. D. Hufford, J. Nat. Prod., 1989, 52, 337.
4. H. J. Liu, W. L. Yeh, and S. Y. Chew, Tetrahedron Lett., 1993, 34, 4435; H. J. Liu, S. Y. Chew, and W. L. Yeh, Youji Huaxue, 1993, 13, 314 (Chem. Abstr., 1994, 120, 8749t).
5. H. J. Liu, W. L. Yeh, and S. Y. Chew, Tetrahedron Lett., 1993, 34, 4435; H. J. Liu, S. Y. Chew, and W. L. Yeh, Youji Huaxue, 1993, 13, 314 (Chem. Abstr., 1994, 120, 8749t).
6. H. J. Liu, W. L. Yeh, and S. Y. Chew, Tetrahedron Lett., 1993, 34, 4435; H. J. Liu, S. Y. Chew, and W. L. Yeh, Youji Huaxue, 1993, 13, 314 (Chem. Abstr., 1994, 120, 8749t).
7. H. J. Liu, S. Y. Chew, and E. N. C. Browne, Tetrahedron Lett., 1991, 32, 2005; H. J. Liu, S. Y. Chew, E. N. C. Browne, and J. B. Kim, Can. J. Chem., 1994, 72, 1993.
8. H. J. Liu, S. Y. Chew, and E. N. C. Browne, Tetrahedron Lett., 1991, 32, 2005; H. J. Liu, S. Y. Chew, E. N. C. Browne, and J. B. Kim, Can. J. Chem., 1994, 72, 1993.
9. For a previous synthesis, see W. S. Zhou, S. J. Xu, and L. Zhang, Acta Chim. Sinica, 1989, 47, 340.
10. R. Rappo, D. S. Allen, Jr., R. U. Lemieux, and W. S. Johnson, J. Org. Chem., 1956, 21, 478.
11. Several other peracids were also examined but the results were inferior.
12. A. B. Smith, III and R. M. Scarborough, Jr., Synth. Commun., 1980, 10, 205; P. H. J. Carlsen, T. Katsuki, V. S. Martin, and K. B. Sharpless, J. Org. Chem., 1981, 46, 3936.
13. A. B. Smith, III and R. M. Scarborough, Jr., Synth. Commun., 1980, 10, 205; P. H. J. Carlsen, T. Katsuki, V. S. Martin, and K. B. Sharpless, J. Org. Chem., 1981, 46, 3936.
14. The yields were based on a single experiment with 17 mg of the starting material. The current study has depleted all the available material and we have not yet had the opportunity to improve this transformation.
15. A. J. Lin, D. L. Klayman, J. M. Hoch, J. V. Silverton, and C. F. George, J. Org. Chem., 1985, 50, 4504.