Steric effects in enyne-allene thermolyses: Switch from the Myers-Saito reaction to the C2-C6-cyclization and DNA strand cleavage

Tetrahedron Letters

Volumn 37, Issue 43, 1996, Pages 7691-7694

  Schmittel, Michael ^a   Kiau, Susanne ^a   Siebert, Torsten ^a   Strittmatter, Marc ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; CYCLIZATION; DNA CLEAVAGE; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0030597031     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01758-3     Document Type: Article

References (21)

1. 1 Thermal and electron transfer induced reactions of enediynes and enyne-allenes, part 6; for part 5 see ref. M. Schmittel, S. Kiau, Chem. Ber., submitted for publication.
2. 2 M. Schmittel, M. Strittmatter, S. Kiau, Tetrahedron Lett. 1995, 36, 4975.
3. 3 M. Schmittel, M. Strittmatter, K. Vollmann, S. Kiau, Tetrahedron Lett. 1996, 37, 999.
4. 4 J. G. Garcia, B. Ramos, L. M. Pratt, A. Rodríguez, Tetrahedron Lett. 1995, 36, 7391.
5. 5 T. Gillmann, T. Hulsen, W. Massa, S. Wocadlo, Synlett 1995, 1257.
6. 6 a) R. Nagata, H. Yamanaka, E. Murahashi, I. Saito, Tetrahedron Lett. 1990, 31, 2907. -
7. b) A. G. Myers, E. Y. Kuo, N. S. Finney, J. Am. Chem. Soc. 1989, 111, 8057.
8. 7 For reviews, see: a) M. E. Maier, Synlett 1995, 13. -
9. b) K. C. Nicolaou, W. M. Dai, Angew. Chem. 1991, 103, 1453; Angew. Chem., Int. Ed. Engl. 1991, 30, 1387.
10. b) K. C. Nicolaou, W. M. Dai, Angew. Chem. 1991, 103, 1453; Angew. Chem., Int. Ed. Engl. 1991, 30, 1387.
11. 8 N. Krause, M. Hohmann, Synlett 1996, 89 and 590.
12. 9 K. C. Nicolaou, P. Maligres, J. Shin, E. de Leon, D. Rideout, J. Am. Chem. Soc. 1990, 112, 7825.
13. 10 M. Schmittel, M. Strittmatter, S. Kiau, Angew. Chem. 1996, 108, 1952 .
14. +1 determined in the gas phase: P. G. Wenthold, S. G. Wierschke, J. J. Nash, R. R. Squires, J. Am. Chem. Soc. 1993, 115, 12611.
15. +1 determined in the gas phase: P. G. Wenthold, S. G. Wierschke, J. J. Nash, R. R. Squires, J. Am. Chem. Soc. 1993, 115, 12611.
16. +1 determined in the gas phase: P. G. Wenthold, S. G. Wierschke, J. J. Nash, R. R. Squires, J. Am. Chem. Soc. 1993, 115, 12611.
17. 12 The synthesis of enyne-allene 2e by another, less efficient strategy has been described in reference 2.
18. H-P = 11.2 Hz, J= 3.4 Hz, 1H), 7.18 (m, 1H), 7.27 (m, 1H), 7.41-7.58 (m, 8H), 7.73-7.88 (m, 4H); IR (neat): ṽ = 2154 (C=C), 1931 (C=C=C).
19. H-P* = 3.2 Hz, 1H), 7.03-7.16 (m, 3H), 7.21-7.30 (m, 2H), 7.34-7.51 (m, 6H), 7.57-7.81 (m, 4H).
20. 15 M. Schmittel, M. Keller, S. Kiau, M. Strittmatter, unpublished results.
21. 1H-NMR spectrum.