Decarboxylative photocyclization: Synthesis of benzopyrrolizidines and macrocyclic lactones

Journal of Organic Chemistry

Volumn 64, Issue 14, 1999, Pages 5213-5217

  Griesbeck, Axel G ^a   Nerowski, Frank ^a   Lex, Johann ^a  

^a UNIVERSITY OF COLOGNE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; BENZOPYRROLIZIDINE DERIVATIVE; LACTONE DERIVATIVE; MACROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; ENANTIOMER; PHOTOCHEMISTRY; STEREOCHEMISTRY; SYNTHESIS; X RAY ANALYSIS;

EID: 0032997444     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990390b     Document Type: Article

References (18)

1. Part of the dissertation of F.N., University of Cologne, 1999.
2. Griesbeck, A. G.; Henz, A.; Peters, K.; Peters, E.-M.; von Schnering, H. G. Angew. Chem. 1995, 107, 498; Angew. Chem., Int. Ed. Engl. 1995, 34, 474.
3. Griesbeck, A. G.; Henz, A.; Peters, K.; Peters, E.-M.; von Schnering, H. G. Angew. Chem. 1995, 107, 498; Angew. Chem., Int. Ed. Engl. 1995, 34, 474.
4. Griesbeck, A. G.; Henz, A.; Kramer, W.; Lex, J.; Nerowski, F.; Oelgemöller, M.; Peters, K.; Peters, E.-M. Helv. Chim. Acta 1997, 80, 912.
5. Takahashi, Y.; Miyashi, T.; Yoon, U. C.; Oh, S. W.; Mancheno, M.; Su, Z.; Falvey, D. F.; Mariano, P. S. J. Am. Chem. Soc. 1999, 121, 3926. Yoon, U. C.; Kim, D. U.; Lee, J. G.; Ammon, H. L.; Mariano, P. S. J. Am. Chem. Soc. 1995, 117, 2698.
6. Takahashi, Y.; Miyashi, T.; Yoon, U. C.; Oh, S. W.; Mancheno, M.; Su, Z.; Falvey, D. F.; Mariano, P. S. J. Am. Chem. Soc. 1999, 121, 3926. Yoon, U. C.; Kim, D. U.; Lee, J. G.; Ammon, H. L.; Mariano, P. S. J. Am. Chem. Soc. 1995, 117, 2698.
7. Yoon, U. C.; Kim, D. U.; Kim, J. C.; Lee, C. W.; Choi, Y. S.; Mariano, P. S.; Lee, Y. J.; Ammon, H. L. Tetrahedron. Lett. 1993, 34, 5859. Yoon, U. C.; Cho, S. J.; Lee, Y.-J.; Mancheno, M. J.; Mariano, P. S. J. Org. Chem. 1995, 60, 2353.
8. Yoon, U. C.; Kim, D. U.; Kim, J. C.; Lee, C. W.; Choi, Y. S.; Mariano, P. S.; Lee, Y. J.; Ammon, H. L. Tetrahedron. Lett. 1993, 34, 5859. Yoon, U. C.; Cho, S. J.; Lee, Y.-J.; Mancheno, M. J.; Mariano, P. S. J. Org. Chem. 1995, 60, 2353.
9. X-ray analyses of rac-3, cis-(+)-3, (+)-4, cis-6a, and 9a. Data collection: Enraf-Nonius-CAD4 diffractometer, Mo Ka graphite monochromator, Wyckoff-scan, θ range (deg) 1.75-27.5. Structural analysis and refinement: solution by direct-phase determination, method of refinement full-matrix LSQ, hydrogen positions of riding model with fixed isotropic U, program used Siemens SHELXL-93.
10. Griesbeck, A. G.; Mauder, H.; Müller, I. Chem. Ber. 1992, 125, 2467.
11. De Koning, H.; Speckamp, W. N. Methods Org. Chem. (Houben-Weyl) 1895, 21b, 1953. Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, 1047.
12. De Koning, H.; Speckamp, W. N. Methods Org. Chem. (Houben- Weyl) 1895, 21b, 1953. Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, 1047.
13. R = 1.2 min.
14. Shono, T.; Matsumura, Y.; Uchida, K.; Kobayashi, J. Org. Chem. 1985, 50, 3243.
15. Smrcina, M.; Majer, P.; Majerová, E.; Guerassina, T. A.; Eissenstat, M. A. Tetrahedron 1997, 53, 12867.
16. Hanus, J.; Tolman, V.; Veres, K. Collect. Czech. Chem. Commun. 1973, 38, 1212.
17. Tseng, C. C. Chem. Pharm. Bull. 1977, 25, 29. = 5a.
18. Okomoto, S. Bull. Chem. Soc. Jpn. 1979, 52, 2670. = 5b.