Stereochemically controlled cyclopropanation of (S)-glyceraldehyde acetonide-derived olefins. Synthesis of (2S,1′R,2′R,3′R)-2-(2′,3′-dicarboxycyclopropyl) glycine

Organic Letters

Volumn 1, Issue 2, 1999, Pages 285-287

  Ma, Dawei ^a   Cao, Yeyu ^a   Yang, Yi ^b   Cheng, Dongliang ^b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001136538     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990598j     Document Type: Article

References (26)

1. (a) Kende, A. S.; Fujii, Y.; Mendoza, J. S. J. Am. Chem. Soc. 1990, 112, 9645.
2. (b) Martin, S. F.; Austin, R. E.; Oalmann, C. J.; Baker, W. R.; Condon, S. L.; deLara, E.; Rosenberg, S. H.; Spina, K. P.; Stein, H. H.; Cohen, J.; Kleinert, H. D. J. Med. Chem. 1992, 35, 1710.
3. (c) Hanessian, S.; Cantin, L.-D.; Roy, S.; Andreotti, D.; Gomtsyan, A. Tetrahedron Lett. 1997, 38, 1103.
4. (d) Braish, T. F.; Castaldi, M.; Chan, S.; Fox, D. F.; Keltonic, T.; McGarry, J.; Hawkins, J. M.; Norris, T.; Rose, P. R.; Sieser, J. E.; Sitter, B. J.; Watson, H., Jr. Synlett 1996, 1100.
5. (e) Pellicciari, R.; Marinozzi, M.; Natalini, B.; Costantino, G.; Luneia, R.; Giorgi, G.; Moroni, F.; Thomsen, C. J. Med. Chem. 1996, 39, 2259.
6. (f) Shimamoto, K.; Ohfune, Y. J. Med. Chem. 1996, 39, 407.
7. (g) Rogers, D. H.; Ti, E. C.; Poulter, C. D. J. Org. Chem. 1995, 60, 941.
8. (h) Bubert, C.; Cabrele, C.; Reiser, O. Synlett 1997, 827.
9. (i) Ohfune, Y.; Shimamoto, K.; Ishida, M.; Shinozaki, H. Bioorg. Med. Chem. Lett. 1993, 3, 15.
10. (j) Norbeck, D. W.; Sham, H. L.; Herrin, T.; Rosenbrook, W.; Plattner, J. J.; J. Chem. Soc., Chem. Commun. 1992, 128.
11. For reviews, see: (a) Doyle, M. P.; Protopova, M. N. Tetrahedron 1998, 54, 7919.
12. (b) Burgess, K.; Ho, K. K.; Moye-Sherman, D. Synlett 1994, 574.
13. (a) Ma, D.; Ma, Z. Tetrahedron Lett. 1997, 38, 7599.
14. (b) Ma, D.; Tian, H.; Zou, G. J. Org. Chem. 1999, 64, 120.
15. (a) Corey, E. J.; Chaykovaky, M. J. Am. Chem. Soc. 1965, 87, 1353.
16. (b) Payne, G. B. J. Org. Chem. 1967, 32, 335.
17. (c) Collado, I.; Dominguez, C.; Ezquerra, J.; Pedregal, C.; Monn, J. A. Tetrahedron Lett. 1997, 38, 2133.
18. For reviews, see: (a) Knopfel, T.; Kuhn, R.; Allgeier, H. J. Med. Chem. 1995, 38, 1418.
19. (b) Ornstein, P. L.; Schoepp, D. D.; Monn, J. A. Curr. Pharm. Des. 1995, 1, 355.
20. (c) Knopfel, T.; Gasparini, F. Drug Discovery Today 1996, 1, 103.
21. (d) Ma, D. Bioorg. Chem. 1999, 27, 20.
22. Krow, G. R. Org. React. 1993, 43, 251.
23. (a) Sauers, R. R.; Ubersax, R. W. J. Org. Chem. 1965, 30, 3939.
24. (b) Emmons, W. D.; Lucas, G. B. J. Am. Chem. Soc. 1955, 77, 2287.
25. (a) Hughes, D. L. Org. React. 1992, 42, 333.
26. (b) Lal, B.; Pramanik, B. N.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1977, 23, 1977.