Synthesis 2012; 44(7): 1102-1108
DOI: 10.1055/s-0031-1290489
paper
© Georg Thieme Verlag Stuttgart · New York

Enantiodivergent Syntheses of Pantolactone and Pantothenic Acid from d-Mannitol

Ishita Sanyal
Department of Chemistry, CSIR–Indian Institute of Chemical Biology, 4 Raja S.C. Mullick Road, Jadavpur, Kolkata 700032, India, Fax: +91(33)24735197   Email: ashisbanerjee@iicb.res.in
,
Piyali Deb Barman
Department of Chemistry, CSIR–Indian Institute of Chemical Biology, 4 Raja S.C. Mullick Road, Jadavpur, Kolkata 700032, India, Fax: +91(33)24735197   Email: ashisbanerjee@iicb.res.in
,
Asish Kumar Banerjee*
Department of Chemistry, CSIR–Indian Institute of Chemical Biology, 4 Raja S.C. Mullick Road, Jadavpur, Kolkata 700032, India, Fax: +91(33)24735197   Email: ashisbanerjee@iicb.res.in
› Author Affiliations
Further Information

Publication History

Received: 26 December 2011

Accepted after revision: 09 February 2012

Publication Date:
05 March 2012 (online)


Abstract

Efficient synthetic routes to both the enantiomers of pantolactone and pantothenic acid have been developed starting from d-mannitol-based d-glyceraldehyde acetonide through its conversion into a protected pantoic acid intermediate followed by either cyclization or amide bond formation with a β-amino ester, and subsequent appropriate deprotection.

 
  • References

  • 1 Stiller ET, Harris SA, Finkelstein J, Keresztesy JC, Folkers K. J. Am. Chem. Soc. 1940; 62: 1785
    • 3a Tokuzaki K, Kanemitu Y, Yoshimitsu T, Nagaoka H. Tetrahedron Lett. 2000; 41: 5923
    • 3b Martin N, Thomas EJ. Tetrahedron Lett. 2001; 42: 8373
    • 3c Ball M, Baron A, Bradshaw B, Omori H, MacCormick S, Thomas EJ. Tetrahedron Lett. 2004; 45: 8737
    • 3d Klar U, Buchmann B, Schwede W, Skuballa W, Hoffmann J, Lichtner RB. Angew. Chem. Int. Ed. 2006; 45: 7942
    • 3e Trost BM, Flygare JA. Tetrahedron Lett. 1994; 35: 4059
    • 3f Nakata T, Fukui H, Nakagawa T, Matsukura H. Heterocycles 1996; 42: 159
    • 3g Sone H, Suenaga K, Bessho Y, Kondo T, Kigoshi H, Yamada K. Chem. Lett. 1998; 85
    • 3h Shiina I, Shibata J, Ibuka R, Imai Y, Mukaiyama T. Bull. Chem. Soc. Jpn. 2001; 74: 113
    • 3i Organ MG, Wang J. J. Org. Chem. 2002; 67: 7847
    • 3j Hajare AK, Datrange LS, Vyas S, Bhuniya D, Reddy DS. Tetrahedron Lett. 2010; 51: 5291
    • 3k Hajare AK, Ravikumar B, Khaleel S, Bhuniya D, Reddy DS. J. Org. Chem. 2011; 76: 963
    • 3l Burns AR, Taylor RJ. K. Synthesis 2011; 681
    • 4a O’Meara JA, Gardee N, Jung M, Ben RN, Durst T. J. Org. Chem. 1998; 63: 3117
    • 4b Hansen MM, Bertsch CF, Harkness AR, Huff BE, Hutchison DR, Khau VV, LeTourneau ME, Martinelli MJ, Misner JW, Peterson BC, Rieck JA, Sullivan KA, Wright IG. J. Org. Chem. 1998; 63: 775
    • 4c For a review on pantolactone, see: Camps P, Muñoz-Torreo D. Curr. Org. Chem. 2004; 8: 1339
    • 5a Lipmann F. Science 1954; 120: 855
    • 5b Shimizu S, Tani Y, Ogata K. Agric. Biol. Chem. 1974; 38: 1989
  • 6 Brody T. Nutritional Biochemistry . 2nd ed. Academic Press; San Diego: 1999
  • 7 Shils ME, Olson JA, Shike M, Ross AC. Modern Nutrition in Health and Diseases . 9th ed. Lippincott Williams & Wilkins; Philadelphia: 1999: 423
  • 8 Leung L. J. Orthomol. Med. 1997; 12: 99
  • 9 Gaddi A, Descovich GC, Noseda G, Fragiacomo C, Colombo L, Craveri A, Montanari G, Sirtori CR. Atherosclerosis (Amsterdam, Neth.) 1984; 50: 73
    • 10a Ebner F, Heller A, Rippke F, Tausch I. Am. J. Clin. Dermatol. 2002; 3: 427
    • 10b Weimann B, Hermann D. Int. J. Vitam. Nutr. Res. 1999; 69: 113
    • 11a Fizet C. Helv. Chim. Acta 1986; 69: 404
    • 11b Fuji K, Node M, Murata M, Terada S, Hashimoto K. Tetrahedron Lett. 1986; 27: 5381
    • 12a Kataoka M, Shimizu K, Sakamoto K, Yamada H, Shimizu S. Appl. Microbiol. Biotechnol. 1995; 43: 974
    • 12b Kesseler M, Friedrich T, Höffken HW, Hauer B. Adv. Synth. Catal. 2002; 344: 1103
    • 13a Roucoux A, Agbossou F, Mortreux A, Petit F. Tetrahedron: Asymmetry 1993; 4: 2279
    • 13b Roucoux A, Devocelle M, Carpentier J.-F, Agbossou F, Mortreux A. Synlett 1995; 358
    • 13c Pasquier C, Naili S, Pelinski L, Brocard J, Mortreux A, Agbossou F. Tetrahedron: Asymmetry 1998; 9: 193
    • 14a Rao AV. R, Rao SM, Sharma GV. M. Tetrahedron Lett. 1994; 35: 5735
    • 14b Upadhay TT, Gurunath S, Sudalai A. Tetrahedron: Asymmetry 1999; 10: 2899
  • 15 Shinkre BA, Rakeeb A, Deshmukh AS. Tetrahedron: Asymmetry 2004; 15: 1081
  • 16 Evans DA, Wu J, Masse CE, Macmillan DW. C. Org. Lett. 2002; 4: 3379
  • 17 Synoradzki L, Rowicki T, Wlostowski M. Org. Process Res. Dev. 2006; 10: 103
  • 18 Kagan F, Heinzelman RV, Weisblat DI, Greiner W. J. Am. Chem. Soc. 1957; 79: 3545
  • 19 Sewell AL, Villa MV, Matheson M, Whittingham WG, Marquez R. Org. Lett. 2011; 13: 800
  • 20 Schmid CR, Bryant JD, Dowlatzedah M, Phillips JL, Prather DE, Schantz RD, Sear NL, Vianco CS. J. Org. Chem. 1991; 56: 4056
    • 21a Dong S, Parker GD, Tei T, Paquette LA. Org. Lett. 2009; 11: 1191
    • 21b Dong S, Parker GD, Tei T, Paquette LA. Org. Lett. 2006; 8: 2429
    • 21c Paquette LA, Parker GD, Tei T, Dong S. J. Org. Chem. 2007; 72: 7125
  • 22 Li J, Sha Y. Molecules 2008; 13: 1111
    • 23a Kido M, Sugiyama S, Satoh T. Tetrahedron: Asymmetry 2007; 18: 1934
    • 23b Mandel AL, La Clair JJ, Burkart MD. Org. Lett. 2004; 6: 4801
  • 24 Mori T, Takahashi K, Kashiwabara M, Uemura D, Katayama C, Iwadare S, Shizuri Y, Mitomo R, Nakano F, Matsuzaki A. Tetrahedron Lett. 1985; 26: 1073