Synthesis and anti-malarial activity of yingzhaosu A analogues from unsaturated hydroperoxy acetals

Tetrahedron Letters

Volumn 41, Issue 17, 2000, Pages 3145-3148

  Tokuyasu, Takahiro ^a   Masuyama, Araki ^a   Nojima, Masatomo ^a   Kim, Hye Sook ^b   Wataya, Yusuke ^b  

^a OSAKA UNIVERSITY   (Japan)

^b OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; UNCLASSIFIED DRUG; YINGZHAOSU A;

ANTIMALARIAL ACTIVITY; ARTICLE; COLUMN CHROMATOGRAPHY; CYCLIZATION; DERIVATIZATION; DRUG SYNTHESIS; IN VITRO STUDY; MALARIA; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0034701597     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00372-5     Document Type: Article

References (12)

1. (a) Zhou, W.-S.; Xu, X.-X. Acc. Chem. Res. 1994, 27, 211.
2. (b) Haynes, R. K.; Vonwiller, S. C. Acc. Chem. Res. 1997, 30, 73.
3. (c) Robert, A.; Meunier, B. Chem. Soc. Rev. 1998, 27, 273. (d) Meshnick, S. R.; Jefford, C. W.; Posner, G. H.; Avery, M. A.; Peters, W. Parasitology Today 1996, 12, 79.
4. Yingzahosu A analogues: (a) O'Neill, P. M.; Searle, N. L.; Raynes, K. J.; Maggs, J. L.; Ward, S. A.; Storr, R. C.; Park, B. K.; Posner, G. H. Tetrahedron Lett. 1998, 39, 6065.
5. Yingzahosu A analogues (b) Balci, M. D.;Korshin, E. E. Synlett, 1998, 122.
6. Yingzahosu A analogues (c) Cazelles, J.; Robert, A.; Meunier, B. J. Org. Chem. 1999, 64, 6776.
7. Ushigoe, Y.; Torao, Y.; Masuyama, A.; Nojima, N. J. Org. Chem. 1997, 62, 4949.
8. Rousseau, G.; Homsi, F. Chem. Soc. Rev. 1997, 26, 453.
9. 2: C, 40.51; H, 5.87; I, 38.91. Found: C, 40.45; H, 5.77; I, 38.99.
10. Halonium ion mediated migration of an alkoxy group in acetals is known: Harding, K. E.; Tiner, T. H. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 4, Chapter 1.9.
11. 5: C, 56.88; H, 8.68. Found: C, 56.88; H, 8.60.
12. Kim, H.-S.; Shibata, Y.; Wataya, Y.; Tsuchiya, K.; Masuyama, A.; Nojima, M. J. Med. Chem. 1999, 42, 2604.