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The Pharmaceutical Society of Korea (대한약학회)
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Diastereoselective Synthesis of Polysubstituted Pyrrolidinone as a Key Intermediate for the Anticancer Agents by Palladium(II)­Catalyzed Carboxylation

  • Published : 2005.02.01
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Abstract

Palladium(II)-catalyzed carboxylation of chiral olefins 6a-d has been examined under various conditions. In the weak basic condition ($K_{2}CO_3$), 7a-d were obtained in good yields. Alternatively, in the strong basic condition, pyrrolidinones 8a-d were obtained resulting in excellent yields and with high diastereoselectivity.

Keywords

References

  1. Harrison, T., Saturated nitrogen heterocycles., Contemp. Org. Synth., 209-224 (1995)
  2. Castelhano, A. L. and Krantz, A., Allenic amino acids. 1. synthesis of $\gamma$-allenic GABA by a novel Aza-cope rearrangement. J. Am. Chem. Soc., 106, 1877-1879 (1984) https://doi.org/10.1021/ja00318a076
  3. Petersen, J. S., Fels, G., and Rapoport, H., Chirospecific synthesis of (+)- and (-)-anatoxin a. J. Am. Chem. Soc., 106, 4539-4547 (1984) https://doi.org/10.1021/ja00328a040
  4. Omura, S., Fujimoto, T., Otoguro, K., Matsuzaki, K., Moriguchi, R., Tanaka, H., and Sasaki, Y., Lactacystin, a novel microbial metabolite, induces neuritogenesis of neuroblastoma cells. J. Antibiot., 44, 113-116 (1991) https://doi.org/10.7164/antibiotics.44.113
  5. Corey, E. J., Li, W., and Richard, G. A., A new magnesiumcatalyzed doubly diastereoselective anti-Aldol reaction leads to a highly efficient process for the total synthesis of lactacystin in quantity. J. Am. Chem. Soc., 120, 2330-2336 (1998) https://doi.org/10.1021/ja973444c
  6. Feling, R. H., Buchanan, G. O., Mincer, T. J., Kauffman, C. A., Jensen, P. R., and Fenical, W., Salinosporamide A: a highly cytotoxic proteasome inhibitor from a novel microbial source, a marine bacterium of the new genus salinospora. Angew. Chem., Int. Ed., 42, 355-357 (2003) https://doi.org/10.1002/anie.200390115
  7. Reddy, L. R., Saravanan, P., and Corey, E. J., A simple stereocontrolled synthesis of salinosporamide A. J. Am. Chem. Soc., 126, 6230-6231 (2004) https://doi.org/10.1021/ja048613p
  8. Asami, Y., Kakeya, H., Onose, R., Yoshida, A., Matsuzaki, H.,and Osada, H., Azaspirene; a novel angiogenesis inhibitor containing a 1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione skeleton produced by the fungus Neosartorya sp. Org. Lett., 4, 2845-2848 (2002) https://doi.org/10.1021/ol020104+
  9. Hayashi, Y., Shoji, M., Yamaguchi, J., Sato, K., Yamaguchi, S., Mukaiyama, T., Sakai, K., Asami, Y., Kakeya, H., and Osada, H., Asymmetric total synthesis of (-)-azaspirene, a novel angiogenesis inhibitor. J. Am. Chem. Soc., 124, 12078- 12079 (2002) https://doi.org/10.1021/ja0276826
  10. Meyers, A. I., Seefeld, M. A., Lefker, B. A., Blake, J. A., and Williard, P. G., Stereoselective alkylation in rigid system. effect of remote substituents on p-facial addition to lactam enolate. stereoelectronic and steric effects. J. Am. Chem.Soc., 120, 7429-7438 (1998) https://doi.org/10.1021/ja980614s
  11. Overman, L. E. and Remarchuk, T. P., Catalytic asymmetric intramolecular aminopalladation; enantioselective synthesis of vinyl-substituted 2-oxazolidinones, 2-imidazolidinones, and 2-pyrrolidinones. J. Am. Chem. Soc., 124, 12-13 (2002) https://doi.org/10.1021/ja017198n
  12. Yoon, C. H., Nagle, A., Chen, C., Gandhi, D., and Jung, K. W., $\gamma$-Lactam synthesis via C-H insertion; elaboration of N-benzyl protecting group for high regioselectivity toward the total synthesis of rolipram. Org. Lett., 5, 2259-2262 (2003) https://doi.org/10.1021/ol0345834
  13. Sun, P. P., Chang, M. Y., Chiang, M. Y., and Chang, N. C., A facile route to polysubstituted N-benzyl pyroglutamates. Org.Lett., 5, 1761-1763 (2003) https://doi.org/10.1021/ol0344164
  14. Huang, P. Q., Wu, T. J., and Ruan, Y. P., A flexible approach to (S)-5-alkyl tetramic acid derivatives; application to the asymmetric synthesis of (+)-preussin and protected (3S, 4S)- AHPPA. Org. Lett., 5, 4341-4344 (2003) https://doi.org/10.1021/ol035617a
  15. Alcaide, B., Almendros, P., and Alonso, J., Synthesis of optically pure highly functionalized $\gamma$-lactams via 2-azetidinonetethered iminophosphoranes. J. Org. Chem., 69, 993-996 (2004) https://doi.org/10.1021/jo035623k
  16. Stille, J. K. and Divakaruni, R., Palladium(II)-catalyzed carboxylation reactions of olefins: scope and utility. J. Org. Chem., 44, 3474-3482 (1979) https://doi.org/10.1021/jo01334a006
  17. Tamaru Y., Hojo, M., and Yoshida, Z., Palladium(II)-catalyzed carbonylation of 3-buten-1-ols and 3-butyn-1-ols: an efficient synthesis of $\gamma$-butyrolactones. J. Org. Chem., 56, 1099-1105 (1991) https://doi.org/10.1021/jo00003a036
  18. Nefkens, S. C., Sperrle, M., and Consiglio, G., Palladiumcatalyzed enantioselective bis-alkoxycarboxylation of olefins. Angew. Chem., Int. Ed., 32, 1719-1720 (1993) https://doi.org/10.1002/anie.199317191
  19. Lee, K. Y., Kim, Y. H., Park, M. S., Oh, C. Y., and Ham, W. H., Stereoselective intramolecular cyclization of allyl and homoallyl benzamide via $\pi$-allylpalladium complex catalyzed by Pd(0). J. Org. Chem., 64, 9450-9458 (1999) https://doi.org/10.1021/jo991065r