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Original Articles

Synthesis of 2-C-Methyl-D-erythritol and 2-C-Methyl-L-threitol; Determination of the Absolute Configuration of 2-C-Methyl-1,2,3,4-butanetetrol Isolated from Phlox sublata L

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Pages 1915-1922 | Received 16 Mar 2000, Accepted 26 Apr 2000, Published online: 22 May 2014

  • 1) Duvold, T., Bravo, J-MC., Grosdemange, P., and Rohmer, M., Biosynthesis of 2-C-methyl-D-erythritol, a putative C5 intermediate in the mevalonate independent pathway for isoprenoid biosynthesis. Tetrahedron Lett., 38, 4769-4772 (1997).
  • 2) Anthonsen, T., Hagen, S., Kazi, S. M. A., Shah, S. W., and Tagar, S., 2-C-methyl-erythritol, a new branched alditol from convolvulus glomerratus. Acta Chem. Scand. B, 30, 91-93 (1976).
  • 3) Dittrich, D. and Angyal, S. J., 2-C-methyl-D-erythritol in leaves of liriodendron tulipifera. Phytochemistry, 27, 935-936 (1988).
  • 4) Ahmed, A. A., Mohamed, H., Effat, A., Mostafa, A., William, H. J., Scott, A. I., Reibenspies, J. H., and Mabry, T. M., A new derivative of glucose and 2-C-methyl-D-erythritol from ferulasinaica. J. Nat. Prod., 59, 1171-1173 (1996).
  • 5) Shah, S. W., Brandange, S., Behr, D., Dahmen, D., Hagen, S., and Anthonsen, T., Absolute configuration of 2-C-methylerythritol from convolvulus glomeratus. Acta Chem. Scand. B, 30, 903 (1976).
  • 6) a) Anthonsen, T., Hagen, S., and Sallam, M. A. E., Synthesis and spectroscopic studies of 2-C-methylerythritol and 2-C-methylthreitol. Phytochemistry, 19, 2375-2377 (1980).
  • 6) b) Ford, C. W., A new lactone from water-stressed Chickpea. Phytochemistry, 20, 2019-2020 (1981).
  • 6) c) Yoshimura, J., Hara, K., Yamamura, M., Mikamine, K., and Hashimoto, K., Branched-chain sugars. XXVIII. Synthesis of 2-C-methyl-L-glyceraldehyde, 2-C-methyl-D-erythrose, and 3-C-methyl-L-erythrose derivatives. Bull. Chem. Soc. Jpn., 55, 933-937 (1982).
  • 6) d) Teresa, J. D. P., Hernandes, J. C., Feliciano, A. S., and Migel del Corral, J. M., Saccharinic acid lactone from Astragallus Lusitanicus Lam. Tetrahedron Lett., 21, 1359-1360 (1980).
  • 6) e) Kobayashi, S., Horibe, H., and Saito, Y., Enantioselective synthesis of both diastereomers, including the α-alkoxy-β-hydroxy- -methyl(phenyl) units, by chiral tin(II) lewis acid-mediated asymmetric aldol reactions. Tetrahedron, 50, 9629-9642 (1994).
  • 7) Kis, K., Wungsintaweekul, J., Eisenreich, W., Zenk, M. H., and Bacher, A., An efficient preparation of 2-C-methyl-D-erythritol 4-phosphoric acid and uts derivatives. J. Org. Chem., 65, 587-592 (2000).
  • 8) Onodera, K., Kashimura, N., and Miyazaki, N., Synthesis of 3-amino-3-deoxy-D-ribose and D-ribose derivatives by means of methylsulfoxide-phosphorus pentaoxide and periodate oxidation. Carbohydr. Res., 21, 159-165 (1972).
  • 9) Sakamoto, I. and Ohrui, H., Biosci. Biotechnol. Biochem., in press.
  • 10) a) Uzawa, H., Nishida, Y., Ohrui, H., and Meguro, H., Application of the diibenzoate chirality method to determine the absolute configuration of glycerols and related acyclic alcohols. J. Org. Chem., 55, 116-122 (1990)
  • 10) b) Harada, N., Saito, A., Ono, A., Gawronski, J., and Gawronski, K., A CD method for determination of the absolute stereochemistry of acyclic glycols. 1. Application of the CD exciton chirality method to acyclic 1,3-dibenzoate sysytem. J. Am. Chem. Soc., 113, 3842-3850 (1991).

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