First synthesis of L-ascorbic acid (vitamin C) from a non-carbohydrate source

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 19, 1998, Pages 3141-3142

  Banwell, Martin ^a   Blakey, Simon ^a   Harfoot, Gwion ^a   Longmore, Robert ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33749114745     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a806062b     Document Type: Article

References (24)

1. P. Ge and K. L. Kirk, J. Org. Chem., 1997, 62, 3340 and references cited therein.
2. F. Mahmoodian, A. Gosiewska and B. Peterkofsky, Arch. Biochem. Biophys., 1996, 336, 86.
3. (a) R. C. Rose and A. M. Bode, FASEB J., 1993, 1135;
4. (b) B. N. Ames, M. K. Shigenaga and T. M. Hagen, Proc. Natl. Acad. Sci. USA, 1993, 90, 7915.
5. M. Csiba, J. Cleophax, S. Petit and S. D. Gero, J. Org. Chem., 1993, 58, 7281 and references cited therein.
6. (a) T. C. Crawford and R. Breitenbach, J. Chem. Soc., Chem. Commun., 1979, 388;
7. (b) T. C. Crawford, US Patent 4,111,958 (1978) (Chem. Abstr., 1979, 90, 138150p).
8. P. Collins and R. Ferrier, Monosaccharides - Their Chemistry and Their Roles in Natural Products, J. Wiley and Sons, Chichester, 1995, pp. 311-312.
9. For an excellent review on "modern methods of monosaccharide synthesis from non-carbohydrate sources" see: T. Hudlicky, D. A. Entwistle, K. K. Pitzer and A. J. Thorpe, Chem. Rev., 1996, 96, 1195.
10. Syntheses of the (±)-modifications of 4-thioascorbic acid and 4-azaascorbic acid from non-carbohydrate starting materials have been reported. See (a) H.-D. Stachel, J. Schachtner and H. Lotter, Tetrahedron, 1993, 49, 4871;
11. (b) H.-D. Stachel, K. Zeitler and H. Lotter, Liebigs Ann. Chem., 1994, 1129.
12. T. Hudlicky and A. J. Thorpe, Chem. Commun., 1996, 1993 and references cited therein.
13. T. Hudlicky, J. Rouden, H. Luna and S. Allen, J. Am. Chem. Soc., 1994, 116, 5099.
14. M. G. Banwell, N. Haddad, T. Hudlicky, T. C. Nugent, M. F. Mackay and S. L. Richards, J. Chem. Soc., Perkin Trans. 1, 1997, 1779.
15. The bromo-analogue of compound 5 has recently been reported: T. Hudlicky, K. A. Abboud, J. Bolonick, R. Maurya, M. L. Stanton and A. J. Thorpe, Chem. Commun., 1996, 1717.
16. T. Ravindranathan, S. V. Hiremath, D. Rajagopala Reddy and A. V. Rama Rao, Carbohydr. Res., 1984, 134, 332.
17. A. M. Felix, E. P. Heimer, T. J. Lambros, C. Tzougraki and J. Meienhofer, J. Org. Chem., 1978, 43, 4194.
18. M. Matsui, M. Okada and M. Ishidate, Yakugaku Zasshi, 1966, 86, 110
19. (Chem. Abstr., 1966, 64, 15967b ).
20. J. Attenburrow, A. F B. Cameron, J. H. Chapman, R. M. Evans, B. A. Hems, A. B. A. Jansen and T. Walker, J. Chem. Soc., 1952, 109 4.
21. (a) R. E. Ireland and L. Liu, J. Org. Chem., 1993, 58, 2899;
22. (b) V. Samano and M. J. Robins, J. Org. Chem., 1990, 55, 5186.
23. M. G. Kulkarni and S. R. Thopate, Tetrahedron, 1996, 52, 1293.
24. W. C. Still, M. Kahn and A. Mitra, J. Org. Chem., 1978, 43, 2923.