Choice of protecting groups for tricarboxylic acids. Synthesis and orthogonal deprotection of 2-carboxysuccinic esters

Synlett

Volumn , Issue 1, 1999, Pages 144-146

  Perrotta, Enzo ^a   Raffaelli, Barbara ^a   Giannotti, Danilo ^a   Harmat, Nicholas J S ^a   Nannicini, Rossano ^a   Altamura, Maria ^a  

^a Menarini Ricerche SpA   (Italy)

Author keywords

Ester protecting groups; Orthogonal deprotection; Tricarboxylic acids

Indexed keywords

ESTER DERIVATIVE; TRICARBOXYLIC ACID;

ARTICLE; ESTERIFICATION; PEPTIDE SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032957164     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2536     Document Type: Article

References (24)

1. a) Christy, M. R.; Barkley, M. R.; Koch, T. H.; Van Buskirk, J.J.; Kirsc, WM J. Am. Chem. Soc. 1981, 103, 3935-3937.
2. b) Shier, W. T.; Habbes, H. K. and Badria, F. A. Tetrahedron Lett. 1995, 36, 1571-1574.
3. c) Aoyama; T.; Sato, T.; Yonemoto, M.; Shibata, J.; Nanoshita, K.; Arai, S.; Kawakami, K.; Iwasawa, Y.; Sano, H.; Tanaka, K.; Monden, Y.; Kodera, T.; Arakawa, H.; Suzuki-Takahashi, I.; Kamei, T.; Tomimoto, K. J. Med. Chem. 1998, 41, 143-147.
4. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; 2nd edition, John Wiley, New York, Toronto, 1991; pp. 224-276. Kocienski, P. J. Protecting Groups, Georg Thieme Verlag, Stuttgart, New York, 1994; pp. 118-154. Vedejs, E.; Wilber, W. R.; Twieg, R. J. Org. Chem. 1977, 42 401-409.
5. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; 2nd edition, John Wiley, New York, Toronto, 1991; pp. 224-276. Kocienski, P. J. Protecting Groups, Georg Thieme Verlag, Stuttgart, New York, 1994; pp. 118-154. Vedejs, E.; Wilber, W. R.; Twieg, R. J. Org. Chem. 1977, 42 401-409.
6. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; 2nd edition, John Wiley, New York, Toronto, 1991; pp. 224-276. Kocienski, P. J. Protecting Groups, Georg Thieme Verlag, Stuttgart, New York, 1994; pp. 118-154. Vedejs, E.; Wilber, W. R.; Twieg, R. J. Org. Chem. 1977, 42 401-409.
7. March, J. Advanced Organic Chemistry, 4th edition, John Wiley, New York, Toronto, 1992; pp. 464-468.
8. ibid. 263-269.
9. Scott, D. M.; McPhail, A. T.; Porter, N.A. Tetrahedron Lett. 1990, 31, 1679-1682.
10. Laurent, J. P.; Morvan, B. J. Chem. Soc., Dalton Trans. 1993, 14, 2141-2146.
11. Salomon, C. J.; Mata, E. G.; Mascaretti, O. A. Tetrahedron Lett. 1991, 32, 4239-4242. Salomon, C. J.; Mata, E. G.; Mascaretti, O. A. Tetrahedron 1993, 49, 3691-3748. Mascaretti, O. A.; Furlan, R. L. E. Aldrichimica Acta 1997, 30, 55-68.
12. Salomon, C. J.; Mata, E. G.; Mascaretti, O. A. Tetrahedron Lett. 1991, 32, 4239-4242. Salomon, C. J.; Mata, E. G.; Mascaretti, O. A. Tetrahedron 1993, 49, 3691-3748. Mascaretti, O. A.; Furlan, R. L. E. Aldrichimica Acta 1997, 30, 55-68.
13. Salomon, C. J.; Mata, E. G.; Mascaretti, O. A. Tetrahedron Lett. 1991, 32, 4239-4242. Salomon, C. J.; Mata, E. G.; Mascaretti, O. A. Tetrahedron 1993, 49, 3691-3748. Mascaretti, O. A.; Furlan, R. L. E. Aldrichimica Acta 1997, 30, 55-68.
14. Kim, S.; Lee, I.J.; Kim, Y. G. J. Org. Chem. 1985, 50, 560-565.
15. -.
16. -.
17. Kaestle, K. L.; Anwer, M. K.; Audhya, T. K.; Goldstein, G. Tetrahedron Lett. 1991, 32, 327-330.
18. +.
19. Kumagai, T.; Abe, T.; Fujimoto, Y.; Hayashi, T.; Inoue, Y.; Nagao, Y. Heterocycles 1993, 36, 1729-1734.
20. Kunz, H.; Unverzagt, C. Angew. Chem., Int. Ed. Engl. 1984, 23, 436-437.
21. -.
22. Hegedus, L. S. Palladium in Organic Synthesis. In Organometallics in Synthesis, a Manual; Schlosser, M., Ed., John Wiley, Chichester, 1994; pp. 383-459. Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257-276.
23. (13) Hegedus, L. S. Palladium in Organic Synthesis. In Organometallics in Synthesis, a Manual; Schlosser, M., Ed., John Wiley, Chichester, 1994; pp. 383-459. Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257-276.
24. Bodanszky, M. Principles of Peptide Synthesis, 2nd edition, Springer, Berlin, Heidelberg, 1993.