Photochemistry of hecogenine acetate revisited

Journal fur Praktische Chemie - Chemiker - Zeitung

Volumn 338, Issue 8, 1996, Pages 695-701

  Jautelat, R ^a   Winterfeldt, E ^a,c   Muller Fahrnow A ^b  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

^b BAYER PHARMA AG   (Germany)

^c LEIBNIZ UNIVERSITY HANNOVER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001249542     PISSN: 09411216     EISSN: None     Source Type: Journal    
DOI: 10.1002/prac.199633801137     Document Type: Article

References (34)

1. a) G. R Pettit, M. Inoue, Y. Kamano, D. L. Herald, C. Arm, C. Dufresne, N. D. Christie, J. M. Schmidt, D. L. Doubek, T. S. Krupa, J. Am. Chem. Soc. 110 (1988) 2006;
2. b) G. R. Pettit, J. Xu, J. M. Schmidt, M. R. Boyd, Bioorg. Med. Chem. Lett 5 (1995) 2027
3. S. Fukuzawa, S. Matsunaga, N. Fusetani, Tetrahedron 51 (1995) 6707
4. a) S. C. Smith, C. H. Heathcock, J. Org. Chem. 57 (1992) 6379;
5. b) C. H. Heathcock, S. C. Smith, J. Org. Chem. 59 (1994) 6828
6. a) Y. Pan, R. L. Merriman, L. R. Tanzer, P. L. Fuchs, Bioorg. Med. Chem. Lett. 9 (1992) 967;
7. b) J. U. Jeong, S. C. Sutton, S. Kim, P. L. Fuchs, J. Am. Chem. Soc. 117 (1995) 10157
8. a) A. Kramer, U. Ullmann, E. Winterfeldt, J. Chem. Soc., Perkin. Trans. 1 1993, 2865;
9. b) For the first biological active cephalostatin analogues see: M. Drögemüller, R. Jautelat, E. Winterfeldt, Angew. Chem. 108 (1996) 1669
10. Römpp Chemie Lexikon, J. Falbe, M. Regitz (eds.), Georg Thieme Verlag, Stuttgart 1992, 4306
11. P. Bladon, W. McMeekin, I. A. Williams, J. Chem. Soc. 1963, 5727
12. P. Welzel, B. Janssen, H. Duddeck, Liebigs Ann. Chem. 1981, 546
13. L. J. Chinn, J. Org. Chem. 32 (1967) 687
14. We thank Prof. Welzel, University of Leipzig, for helpful discussions.
15. J. A. Porco jr., S. L. Schreiber: The Paternò-Büchi Reaction, in: Comprehensive Organic Synthesis, B. M. Trost (ed.), vol. 5, Pergamon Press 1991
16. a) H. W. Scheeren, R. W. M. Aben, P. H. J. Ooms, R. J. F. Nivard, J. Org. Chem. 42 (1977) 3128;
17. b) J. Mattay, K. Buchkremer, Heterocycles 27 (1988) 2153
18. a) Y. R. Naves, P. Ochsner, Helv. Chim. Acta 47 (1964) 51 and lit. cited therein;
19. b) B. C. Clark jr., C. C. Powell, T. Radford, Tetrahedron 33 (1977) 2187
20. a) B. G. Saucy, R. E. Ireland, J. Bordner, R. E. Dickerson, J. Org. Chem. 36 (1971) 1195;
21. b) J. A. Marschall, P. G. M. Wuts, J. Am. Chem. Soc. 100 (1978) 1627;
22. c) E. J. Corey, D. L. Bogner, Tetrahedron Lett. 1978, 2461;
23. d) A. Itoh, K. Oshima, H. Nozaki, Tetrahedron Lett. 1979, 1783
24. a) B. B. Snider, M. Karras, R. T. Price, D. J. Rodini, J. Org. Chem 47 (1982) 4538;
25. b) A. B. Smith III, M. Fukui, H. A. Vaccaro, J. R. Empfield, J. Am. Chem. Soc. 113 (1991) 2071;
26. c) K. Mikami, M. Terada, E. Sawa, T. Nakai, Tetrahedron Lett. 1991, 6571
27. a) M. I. Johnston, J. A. Kwass, R. B. Seal, B. B. Snider, J. Org. Chem. 52 (1987) 5419;
28. b) T. Ooi, K. Maruoka, H. Yamamoto, Tetrahedron 50 (1994) 6505
29. For reviews see: a) H. M. R. Hoffmann, Angew. Chem. 81 (1969) 597,
30. Angew. Chem., Int. Ed. Engl. 8 (1969) 556;
31. b) W. Oppolzer, V. Snieckus, Angew. Chem. 90 (1978) 506,
32. Angew. Chem., Int. Ed. Engl. 17 (1978) 476;
33. c) B. B. Snider, Acc. Chem. Res 13 (1980) 426
34. E. Winterfeldt: Stereocontrolled Organic Synthesis, B. M. Trost (ed.), Blackwell Scientific Publications 1994, 275