Retro-Diels-Alder reaction using bicyclo[2.2.2]octatriene-fused pyrrole during porphyrin synthesis

Tetrahedron Letters

Volumn 48, Issue 44, 2007, Pages 7825-7828

  Uno, Hidemitsu ^a,b   Sahara, Yuri ^a,b   Takiue, Takahiro ^a,b  

^a Integrated Center for Sciences   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Bicyclo 2.2.2 octatriene; Porphyrin synthesis; Retro Diels Alder reaction

Indexed keywords

BICYCLO COMPOUND; BICYCLO[2.2.2]OCTATRIENE; PORPHYRIN; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DIELS ALDER REACTION; REACTION ANALYSIS; SYNTHESIS;

ALNUS;

EID: 34848905625     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.09.004     Document Type: Article

References (22)

1. For reviews, see:. Lindsey J.L. In: Kadish K.M., Smith K.M., and Guilard R. (Eds). The Porphyrin Handbook Vol. 1, Chapter 2 (2000), Academic Press, New York
2. Smith K.M. In: Kadish K.M., Smith K.M., and Guilard R. (Eds). The Porphyrin Handbook Vol. 1, Chapter 1 (2000), Academic Press, New York
3. Shanmugathasan S., Edwards C., and Boyle R.W. Tetrahedron 56 (2000) 1025-1046
4. Mauzerall D. In: Dolphin D. (Ed). The Porphyrins Vol. 2, Chapter 3 (1978), Academic Press, New York
5. Smith K.M. Porphyrins and Metalloporphyrins (1975), Elsevier, Amsterdam
6. Uno H., Inoue K., Inoue T., and Ono N. Org. Biomol. Chem. 1 (2003) 3857-3863 and references cited therein
7. Sessler J.L., Zimmerman R.S., Bucher C., Král V., and Andrioletti B. Pure Appl. Chem. 73 (2001) 1033-1145
8. and also see:. Liu C., Shen D.-M., and Chen Q.-Y. J. Am. Chem. Soc. 129 (2007) 5814-5815
9. Sergeeva N.N., and Senge M.O. Tetrahedron Lett 47 (2006) 6169-6172
10. Senge M.O., Kalisch W.W., and Bischoff I. Chem. Eur. J 6 (2000) 2721-2738
11. Bonomo L., Solari E., Scopelliti R., Floriani C., and Re N. J. Am. Chem. Soc. 122 (2000) 5312-5326
12. Yamada H., Kushibe K., Okujima H., Uno H., and Ono H. Chem. Commun. (2006) 383-384
13. Carruthers W., and Coldham I. Modern Methods of Organic Synthesis. 4th ed. (2007), Cambridge University Press, Cambridge
14. Uno H., Ishikawa T., Hoshi T., and Ono N. Tetrahedron Lett. 44 (2003) 5163-5165
15. Corey E.J., and Hopkins P.B. Tetrahedron Lett. 23 (1982) 1979-1982
16. Baran A., Secen H., and Balci M. Synthesis 10 (2003) 1500-1502
17. van Tamelen E.E. J. Am. Chem. Soc. 77 (1955) 1705-1706
18. Vögel E., and Gunther H. Angew. Chem., Int. Ed. Engl. 6 (1967) 386-387
19. Cossu S., Battaggia S., and de Lucchi O. J. Org. Chem. 62 (1997) 4162-4163
20. Uno H., Nakamoto K., Kuroki K., Fujimoto A., and Ono N. Chem. Eur. J. 13 (2007) 5773
21. Burns D.H., Caldwell T.M., and Burden M.W. Tetrahedron Lett. 34 (1993) 2883-2886
22. Uno, H.; Shimizu, Y.; Uoyama, H.; Tanaka, T.; Okujima, T.; Ono, N. Eur. J. Org. Chem. 2007. doi:10.1002/ejoc.200700700711.