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DOI: 10.1039/A607158I (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 1013-1016

D-Erythronolactone as a C4 building unit. Part 2.1 A short and efficient synthesis of both enantiomers of epi-muricatacin, a diastereoisomer of the native acetogenin from Annona muricata

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Andreas Gypser, Marcus Peterek and Hans-Dieter Scharf

Abstract

Both enantiomers of epi-muricatacin (+)- and (-)-2 have been prepared from 2,3-O-isopropylidene-D-erythrose 7. The enantiomers (+)- and (-)-2 are obtained in good yields and with high diastereoisomeric and enantiomeric purity. The aim of the synthesis is to obtain both enantiomers of the target molecule from one chiral precursor. This was made possible by the reaction sequence for the introduction of the two different side chains being exchangeable.

References

  1. A. Gypser, M. Flasche and H.-D. Scharf, Liebigs Ann., 1994, 775 Search PubMed.
  2. M. Rieser, J. F. Kozlowski, K. V. Wood and J. L. McLaughlin, Tetrahedron Lett., 1991, 32, 1137 CrossRef CAS.
  3. B. Figadère, J.-C. Harmange, A. Laurens and A. Cavé, Tetrahedron Lett., 1991, 32, 7539 CrossRef CAS.
  4. (a) C. Bonini, C. Federici, L. Rossi and G. Righi, J. Org. Chem., 1995, 60, 4803 CrossRef CAS; (b) C. Gravier-Pelletier, M. Sanière, I. Charvet, Y. Le Merrer and J.-C. Depezay, Tetrahedron Lett., 1994, 35, 115 CrossRef CAS.
  5. S. K. Kang, H. S. Cho, H. S. Sim and B. K. Kim, J. Carbohydr. Chem., 1992, 11, 807 CAS.
  6. J. A. Marshall and G. Welmaker, Synlett, 1992, 537 CrossRef CAS.
  7. G. Scholz and W. Tochtermann, Tetrahedron Lett., 1991, 32, 5535 CrossRef CAS.
  8. W. Tochtermann, G. Scholz, G. Bunte, C. Wolff, E. Peters, K. Peters and H. G. von Schnering, Liebigs Ann., 1992, 1069 Search PubMed.
  9. Z.-M. Wang, X. L. Zhang and K. B. Sharpless, Tetrahedron Lett., 1992, 33, 6407 CrossRef CAS.
  10. M. Saiah, M. Bessodes and K. Antonakis, Tetrahedron Lett., 1993, 34, 1597 CrossRef CAS.
  11. A. Gypser, 1995, Ph.D. Thesis, RWTH Aachen.
  12. M. Flasche, Tetrahedron Asym., 1995, 6, 1543 Search PubMed.
  13. M. Flasche, 1994, Ph.D. Thesis, RWTH Aachen.
  14. N. Cohen, B. Banner, R. Lopresti, F. Wong, M. Rosenberger, Y. Liu, E. Thom and A. Liebman, J. Am. Chem. Soc., 1983, 105, 3661 CrossRef CAS.
  15. N. Cohen, B. L. Banner, A. J. Laurenzano and L. Carozza, Organic Synth., 1984, 63, 127 Search PubMed.
  16. Autorenkollektiv, VEB Deutscher Verlag der Wissenschaften, Berlin, 1976.
  17. K. E. Pfitzner and J. G. Moffat, J. Am. Chem. Soc., 1965, 5661 CrossRef CAS.
  18. J. G. Moffat, Organic Synth., Coll. Vol. V, 1973, 242 Search PubMed.
  19. J. E. Baldwin, Tetrahedron, 1982, 38, 2939 CrossRef CAS.