Expeditious biomimetically-inspired approaches to racemic homocitric acid lactone and per-homocitrate

Tetrahedron

Volumn 63, Issue 10, 2007, Pages 2148-2152

  Chen, Hong Bin ^a   Chen, Ling Yan ^a   Huang, Pei Qiang ^a   Zhang, Hong Kui ^a   Zhou, Zhao Hui ^a   Tsai, Khi Rui ^a  

^a XIAMEN UNIVERSITY   (China)

Author keywords

Allylation; Homocitric acid; Homocitric acid lactone; Indium; Per homocitric acid

Indexed keywords

CARBONYL DERIVATIVE; CITRIC ACID; CITRIC ACID TRIETHYL ESTER; INDIUM; LACTONE;

ALLYLATION; ARTICLE; BIOMIMETICS; METHYLATION; PRIORITY JOURNAL; RACEMIZATION;

EID: 33846796070     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.12.092     Document Type: Article

References (52)

1. Burgess B.K., and Lowe D.J. Chem. Rev. 96 (1996) 2983-3011
2. Hoover T.R., Robertson A.D., Cerny R.L., Hayes R.N., Imperial J., Shah V.K., and Ludden P.W. Nature 329 (1987) 855-857
3. Hoover T.R., Imperial J.P., Ludden W., and Shah V.K. Biochemistry 28 (1989) 2768-2771
4. Kim J., and Rees D.C. Science 257 (1992) 1677-1682
5. Zabriskie T.M., and Jackson M.D. Nat. Prod. Rep. 17 (2000) 85-97
6. Suvarna K., Seah L., Bhattacharjee V., and Bhattacharjee J.K. Curr. Genet. 33 (1998) 268-275
7. Palmer D.R.J., Balogh H., Ma G., Zhou X., Marko M., and Kaminskyj S.G.W. Pharmazie 59 (2004) 93-98
8. For racemic synthesis of homocitric acid lactone, see:
9. Maragoudakis M.E., and Strassman M. J. Biol. Chem. 241 (1966) 695-699
10. Tucci A.F., Ceci L.N., and Bhattacharjee J.K. Methods Enzymol. 13 (1969) 619-623
11. Li Z.-C., and Xu J.-Q. Molecules 3 (1998) 31-34
12. For a racemic synthesis followed by resolution, see:
13. Ancliff R.A., Russell A.T., and Sanderson A.J. Tetrahedron: Asymmetry 8 (1997) 3379-3382
14. For chiral synthesis, see:. Thomas U., Kalyanpur M.G., and Stevens C.M. Biochemistry 5 (1966) 2513-2516 See also:
15. Tavassoli A., Duffy J.E.S., and Young D.W. Tetrahedron Lett. 46 (2005) 2093-2096
16. For asymmetric synthesis of homocitric acid lactone, see:. Rodriguez G.H.R., and Biellmann J.F. J. Org. Chem. 61 (1996) 1822-1824
17. Ma G., and Palmer D.R.J. Tetrahedron Lett. 41 (2000) 9209-9212
18. Xu P.-F., Matsumoto T., Ohki Y., and Tatsumi K. Tetrahedron Lett. 46 (2005) 3815-3818
19. Paju A., Kanger T., Pehk T., Eek M., and Lopp M. Tetrahedron 60 (2004) 9081-9084
20. Huang P.-Q., and Li Z.-Y. Tetrahedron: Asymmetry 16 (2005) 3367-3370
21. For an asymmetric synthesis of a precursor of (S)-per-homocitric acid, see Ref. 7e.
22. Tsai K.R., and Wan H.L. J. Cluster Sci. 6 (1995) 485-501
23. Zhou Z.H., Wan H.L., and Tsai K.R. Inorg. Chem. 39 (2000) 59-64
24. Zhou Z.H., Hou S.Y., Cao Z.X., Tsai K.R., and Chow Y.L. Inorg. Chem. 45 (2006) 8447-8451
25. Strassman M., and Ceci L.N. Biochem. Biophys. Res. Commun. 14 (1964) 262-267
26. Strassman M., and Ceci L.N. J. Biol. Chem. 240 (1965) 4357-4361
27. Hogg R.W., and Broquist H.P. J. Biol. Chem. 243 (1968) 1839-1845
28. Loh T.-P., Huang J.-M., Goh S.-H., and Vittal J.J. Org. Lett. 2 (2000) 1291-1294
29. Nakamura S., Sato H., Hirata Y., Watanabe N., and Hashimoto S. Tetrahedron 61 (2005) 11078-11106
30. Roers R., and Verdine G.L. Tetrahedron Lett. 42 (2001) 3563-3565
31. Carlsen P.H.J., Katsuki T., Martin V.S., and Sharpless K.B. J. Org. Chem. 46 (1981) 3936-3938
32. For allyl metal addition to α-keto-esters or α-keto-amides, see:
33. Soai K., and Ishizaki M. J. Org. Chem. 51 (1986) 3290-3295
34. Kiegiel K., and Jurczak J. Tetrahedron Lett. 40 (1999) 1009-1012
35. Loh T.-P., Huang J.-M., Xu K.-C., Goh S.-H., and Vittal J.J. Tetrahedron Lett. 41 (2000) 6511-6515
36. Shin J.A., Cha J.H., Pae A.N., Choi K.I., Koh H.Y., Kang H.-Y., and Cho Y.S. Tetrahedron Lett. 42 (2001) 5489-5492
37. Basavaiah D., and Sreenivasulu B. Tetrahedron Lett. 43 (2002) 2987-2990
38. Kaur P., Singh P., and Kumar S. Tetrahedron 61 (2005) 8231-8240
39. Chen J.H., Venkatesham U., Lee L.C., and Chen K.M. Tetrahedron 62 (2006) 887-893
40. For a review on selective reactions using allylic metals, see:. Yamamoto Y. Chem. Rev. 93 (1993) 2207-2293
41. For reviews, see:
42. Li C.-J., and Chan T.-K. Tetrahedron 55 (1999) 1149-1176
43. Ranu B.C. Eur. J. Org. Chem. (2000) 2347-2356
44. Pae A.M., and Cho Y.-S. Curr. Org. Chem. 6 (2002) 715-737
45. Podlech J., and Maier T.C. Synthesis (2003) 633-655
46. Nair V., Ros S., Jayan C.N., and Pillai B. Tetrahedron 60 (2004) 1959-1982
47. Li C.-J. Chem. Rev. 105 (2005) 3095-3165
48. Loh T.P., and Chua G.L. J. Synth. Org. Chem. Jpn. 63 (2005) 1137-1146
49. During the progress of this work, an interesting indium-mediated allylation of α-oxo-glutaric acid leading to lactone was reported, see:. Singh P., Mittal A., Kaur P., and Kumar S. Tetrahedron 62 (2006) 1063-1068
50. Zimmermann F., Mend E., and Oget N. Tetrahedron Lett. 46 (2005) 3201-3203
51. Yeh M.-C., Sheu B.-A., Fu H.-W., Tau S.-I., and Chuang L.-W. J. Am. Chem. Soc. 115 (1993) 5941-5952
52. While this work is in progress, a concise Reformatsky reaction-based synthesis followed by optical resolution of homocitric acid lactone was described, in which harmful benzene was used as a solvent:. Jia Y.-H., Palmer D.R.J., and Quail J.W. Acta Crystallogr. E61 (2005) o4034-o4036