4-Formylazetidin-2-ones, synthon for the synthesis of (2R,3S) and (2S,3R)-3-amino-2-hydroxydecanoic acid (AHDA)

Tetrahedron

Volumn 62, Issue 18, 2006, Pages 4615-4621

  Shirode, Nilesh M ^a   Deshmukh, Abdul Rakeeb A S ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Amino acids; Azetidin 2 ones; Staudinger reaction; Stereoselective synthesis; Wittig reaction

Indexed keywords

3 AMINO 2 HYDROXYDECANOIC ACID; 3 BENZYLOXY 4 FORMYLAZETIDIN 2 ONE; AZETIDINONE DERIVATIVE; DECANOIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ENANTIOMER; PRIORITY JOURNAL; SYNTHESIS;

EID: 33748672092     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.01.082     Document Type: Article

References (63)

1. For reviews on β-lactam antibiotics, see: (a). Dürkheimer W., Blumbach J., Lattrell R., and Scheunemann K.H. Angew. Chem., Int. Ed. Engl. 24 (1985) 180-202
2. In: Morin R.B., and Gorman M. (Eds). Chemistry and Biology of β-Lactam Antibiotics Vols. 1-3 (1982), Academic, New York
3. Coulton S., and Hunt E. In: Lukacs G. (Ed). Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products Vol. 2 (1993), Springer, Berlin 621
4. Southgate R. Contemp. Org. Synth. 1 (1994) 417-431
5. In: Page M.I. (Ed). The Chemistry of β-lactams (1992), Chapman and Hall, London
6. For comprehensive general reviews, see: (a). Koppel G.A. In: Hasner A. (Ed). Small Ring Heterocycles Vol. 42 (1983), Wiley, New York 219
7. Backes J. In: Muller E., and Bayer O. (Eds). Houben-Weyl, Methoden der Organischem Chemie (1991), Thieme, Stuttgart 31 Band E16B
8. de Kimpe N. In: Katritzky A.R., Rees C.W., Scriven E.F.V., and Padwa A. (Eds). Comprehensive Heterocyclic Chemistry II Vol. 1B (1996), Pergamon, Oxford 507
9. Ojima I. In: Georg G.I. (Ed). The Chemistry of β-Lactams (1993), VCH, New York 197 and references cited therein
10. Palomo C., Aizpurua J., and Ganboa I. In: Juaristi E. (Ed). Enantioselective Synthesis of Beta-Amino Acids (1997), Wiley-VCH, New York 279-357 and references cited therein
11. (c) For a review on this subject see:. Ojima I., and Delaloge F. Chem. Soc. Rev. 26 (1997) 377-386
12. Alcaide B., and Almendros P. Chem. Soc. Rev. 30 (2001) 226-240
13. Alcaide B., and Almendros P. Synlett (2002) 381-393
14. Nagahara T., and Kametani T. Heterocycles 25 (1987) 729-806
15. Thomas R.C. In: Lukacs G., and Ohno M. (Eds). Recent Progress in the Chemical Synthesis of Antibiotics (1990), Springer, Berlin 553
16. Palomo C. In: Lukacs G., and Ohno M. (Eds). Recent Progress in the Chemical Synthesis of Antibiotics (1990), Springer, Berlin 565
17. Palomo C., Arrieta A., Cossio F.P., Aizpurua J.M., Mielgo A., and Aurrekoetxea N. Tetrahedron Lett. 31 (1990) 6429-6432
18. Palomo C., Cabre F., and Ontoria J.M. Tetrahedron Lett. 33 (1992) 4819-4822
19. Annunziata R., Benaglia M., Cinquini M., Cozzi F., and Ponzini F. J. Org. Chem. 58 (1993) 4746-4748
20. Alcaide B., and Almendros P. Chem. Soc. Rev. 30 (2001) 226-240
21. Jayaraman M., Deshmukh A.R.A.S., and Bhawal B.M. J. Org. Chem. 59 (1994) 932-934
22. Jayaraman M., Nandi M., Sathe K.M., Deshmukh A.R.A.S., and Bhawal B.M. Tetrahedron: Asymmetry 4 (1993) 609-612
23. Jayaraman M.J., Deshmukh A.R.A.S., and Bhawal B.M. Tetrahedron 52 (1996) 8989-9004
24. Krishnaswamy D., Govande V.V., and Deshmukh A.R.A.S. Synthesis 12 (2003) 1903-1908
25. Govande V.V., Arun M., Deshmukh A.R.A.S., and Bhawal B.M. Synth. Commun. 30 (2000) 4177-4182
26. Joshi S.N., Deshmukh A.R.A.S., and Bhawal B.M. Tetrahedron: Asymmetry 11 (2000) 1477-1485
27. Krishnaswamy D., Bhawal B.M., and Deshmukh A.R.A.S. Tetrahedron Lett. 41 (2000) 417-419
28. Thiagarajan K., Puranik V.G., Deshmukh A.R.A.S., and Bhawal B.M. Tetrahedron 56 (2000) 7811-7816
29. Karupaiyan K., Puranik V.G., Deshmukh A.R.A.S., and Bhawal B.M. Tetrahedron 56 (2000) 8555-8560
30. Bhawal B.M., Joshi S.N., Krishnaswamy D., and Deshmukh A.R.A.S. J. Indian Inst. Sci. 81 (2001) 265-276
31. Joshi S.N., Puranik V.G., Deshmukh A.R.A.S., and Bhawal B.M. Tetrahedron: Asymmetry 12 (2001) 3073-3076
32. Arun M., Govande V.V., Deshmukh A.R.A.S., and Bhawal B.M. Indian J. Chem. 41B (2002) 856-857
33. Krishnaswamy D., Govande V.V., Gumaste V.K., Bhawal B.M., and Deshmukh A.R.A.S. Tetrahedron 58 (2002) 2215-2225
34. Patil R.T., Parveen G., Gumaste V.K., Bhawal B.M., and Deshmukh A.R.A.S. Synlett (2002) 1455-1458
35. Joshi S.N., Phalgune U.D., Bhawal B.M., and Deshmukh A.R.A.S. Tetrahedron Lett. 44 (2003) 1827-1830
36. Arun M., Joshi S.N., Puranik V.G., Bhawal B.M., and Deshmukh A.R.A.S. Tetrahedron 59 (2003) 2309-2316
37. Shinkre B.A., Puranik V.G., Bhawal B.M., and Deshmukh A.R.A.S. Tetrahedron: Asymmetry 14 (2003) 453-459
38. Jayanthi A., Gumaste V.K., and Deshmukh A.R.A.S. Synlett (2004) 979-982
39. Shaikh A.L., Puranik V.G., and Deshmukh A.R.A.S. Tetrahedron 61 (2005) 2441-2451
40. Jayaraman M., Puranik V.G., and Bhawal B.M. Tetrahedron 52 (1996) 9005-9016
41. Srirajan V., Deshmukh A.R.A.S., Puranik V.G., and Bhawal B.M. Tetrahedron: Asymmetry 7 (1996) 2733-2738
42. Deshmukh A.R.A.S., Bhawal B.M., Krishnaswamy D., Govande V.V., Shinkre B.A., and Jayanthi A. Curr. Med. Chem. 11 (2004) 1889-1920
43. Shirode N.M., Kulkarni K.C., Gumaste V.K., and Deshmukh A.R.A.S. ARKIVOC (i) (2005) 53-64
44. Okino T., Matsuda H., Murakami M., and Yamaguchi K. Tetrahedron Lett. 34 (1993) 501-504
45. Ishida K., Kato T., Murakami M., Watanabe M., and Watanabe M.F. Tetrahedron 56 (2000) 8643-8656
46. Ishida K., Matsuda H., and Murakami M. Tetrahedron 54 (1998) 13475-13484
47. Matsuura F., Hamada Y., and Shioiri T. Tetrahedron 50 (1994) 11303-11314
48. Bunnage M.E., Burke A.J., Davies S.G., and Goodwin C.J. Tetrahedron: Asymmetry 6 (1995) 165-176
49. Wee A.G.H., and McLeod D.D. J. Org. Chem. 68 (2003) 6268-6273
50. Ha H.J., Ahn Y.-G., Woo J.-S., Lee G.S., and Lee W.K. Bull. Chem. Soc. Jpn. 74 (2001) 1667-1672
51. Bergmeier S.C., and Stanchina D.M. J. Org. Chem. 64 (1999) 2852-2859
52. Sugimura H., Miura M., and Yamada N. Tetrahedron: Asymmetry 8 (1997) 4089-4099
53. Righi G., Chionne A., D'Achille R., and Bonini C. Tetrahedron: Asymmetry 8 (1997) 903-907
54. Jefford C.W., Mcnulty J., Lu Z.H., and Wang J.B. Helv. Chim. Acta 79 (1996) 1203-1216
55. Tuch A., Saniere M., Merrer Y.L., and Depezay J. Tetrahedron: Asymmetry 7 (1996) 2901-2909
56. Bunnage M.E., Burke A.J., Davies S.G., and Goodwin C.J. Tetrahedron: Asymmetry 5 (1994) 203-206
57. Palomo C., Aizpurua J., Ganboa I., and Oiarbide M. Synlett (2001) 1813-1826
58. Banik B.K., Manhas M.S., Kaluza Z., Barakat K.J., and Bose A.K. Tetrahedron Lett. 33 (1992) 3603-3606
59. Wagle D.R., Garai C., Chiang J., Monteleone M.G., Kurys B.E., Strohmeyer T.M., Hegde V.R., Manhas M.S., and Bose A.K. J. Org. Chem. 53 (1988) 4227-4236
60. Andrews G.C., Crawford T.C., and Bacon B.E. J. Org. Chem. 46 (1981) 2977-2979
61. Hubschwerlen C. Synthesis (1986) 962-964
62. Kronenthal D.R., Han C.Y., and Taylor M.K. J. Org. Chem. 47 (1982) 2765-2768
63. Bieg T., and Szeja W. Synthesis (1985) 76-77