Current advances in the chemical synthesis of annonaceous acetogenins and relatives

Chemtracts

Volumn 11, Issue 11, 1998, Pages 803-827

  Casiraghi, Giovanni ^b   Zanardi, Franca ^b   Battistini, Lucia ^b   Rassu, Gloria ^b   Appendino, Giovanni ^b  

^a UNIVERSITY OF PARMA   (Italy)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

ACETOGENIN; UNCLASSIFIED DRUG; UVARICIN;

DRUG CONFORMATION; DRUG ISOLATION; DRUG SYNTHESIS; SHORT SURVEY; STRUCTURE ACTIVITY RELATION;

EID: 0031769362     PISSN: 14319268     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Short Survey

References (31)

1. The term annonaceous acetogenins is rooted in the literature, but AJ. Birch, the discoverer of the polyketide pathway, cogently argued that the use of "acetogenins" to refer to polyketides is wrong from the point of view of semantics, chemistry, biochemistry, and priority. Birch, A.J. To See the Obvious, American Chemical Society: Washington, D.C., 1995, pp. 139-140. For proper reference on the Annonaceae see: Mabberley, D.J. In Flowering Plants of the World, Heywood, V.H., ed. Oxford University Press: Oxford, 1978, pp. 30-31. Useful databases on this subject are also available using the AltaVista digital internet service at http://altavista.digital.com/.
2. The term annonaceous acetogenins is rooted in the literature, but AJ. Birch, the discoverer of the polyketide pathway, cogently argued that the use of "acetogenins" to refer to polyketides is wrong from the point of view of semantics, chemistry, biochemistry, and priority. Birch, A.J. To See the Obvious, American Chemical Society: Washington, D.C., 1995, pp. 139-140. For proper reference on the Annonaceae see: Mabberley, D.J. In Flowering Plants of the World, Heywood, V.H., ed. Oxford University Press: Oxford, 1978, pp. 30-31. Useful databases on this subject are also available using the AltaVista digital internet service at http://altavista.digital.com/.
3. For reviews, book chapters, and general accounts on this and related topics, see the references listed at the end of the article. See also: McLaughlin, J.L., Chang, C., Smith, D.L. In Human Medicinal Agents from Plants, Kinghorn, A.D., Baladrin, M.F., eds. Americal Chemical Society: Washington, D.C., 1993, Chap. 9, p. 117; Ramirez, E.A., Hoye, T.R. In Studies in Natural Products Chemistry, Structure and Chemistry, Part D, Atta-ur-Rahman, ed. Elsevier: New York, 1995, Vol. 17, p. 251; Figadère, B., Cave, A. In Studies in Natural Products Chemistry, Stereoselective Synthesis, Atta-ur-Rahman, ed. Elsevier: Amsterdam, 1996, Vol. 18, p. 193; Zafra-Polo, M.C., Gonzalez, M.C., Estornell, E., Sahpaz, S., Cortes, D. Phytochemistry 1996, 42, 253.
4. For reviews, book chapters, and general accounts on this and related topics, see the references listed at the end of the article. See also: McLaughlin, J.L., Chang, C., Smith, D.L. In Human Medicinal Agents from Plants, Kinghorn, A.D., Baladrin, M.F., eds. Americal Chemical Society: Washington, D.C., 1993, Chap. 9, p. 117; Ramirez, E.A., Hoye, T.R. In Studies in Natural Products Chemistry, Structure and Chemistry, Part D, Atta-ur-Rahman, ed. Elsevier: New York, 1995, Vol. 17, p. 251; Figadère, B., Cave, A. In Studies in Natural Products Chemistry, Stereoselective Synthesis, Atta-ur-Rahman, ed. Elsevier: Amsterdam, 1996, Vol. 18, p. 193; Zafra-Polo, M.C., Gonzalez, M.C., Estornell, E., Sahpaz, S., Cortes, D. Phytochemistry 1996, 42, 253.
5. For reviews, book chapters, and general accounts on this and related topics, see the references listed at the end of the article. See also: McLaughlin, J.L., Chang, C., Smith, D.L. In Human Medicinal Agents from Plants, Kinghorn, A.D., Baladrin, M.F., eds. Americal Chemical Society: Washington, D.C., 1993, Chap. 9, p. 117; Ramirez, E.A., Hoye, T.R. In Studies in Natural Products Chemistry, Structure and Chemistry, Part D, Atta-ur-Rahman, ed. Elsevier: New York, 1995, Vol. 17, p. 251; Figadère, B., Cave, A. In Studies in Natural Products Chemistry, Stereoselective Synthesis, Atta-ur-Rahman, ed. Elsevier: Amsterdam, 1996, Vol. 18, p. 193; Zafra-Polo, M.C., Gonzalez, M.C., Estornell, E., Sahpaz, S., Cortes, D. Phytochemistry 1996, 42, 253.
6. For reviews, book chapters, and general accounts on this and related topics, see the references listed at the end of the article. See also: McLaughlin, J.L., Chang, C., Smith, D.L. In Human Medicinal Agents from Plants, Kinghorn, A.D., Baladrin, M.F., eds. Americal Chemical Society: Washington, D.C., 1993, Chap. 9, p. 117; Ramirez, E.A., Hoye, T.R. In Studies in Natural Products Chemistry, Structure and Chemistry, Part D, Atta-ur-Rahman, ed. Elsevier: New York, 1995, Vol. 17, p. 251; Figadère, B., Cave, A. In Studies in Natural Products Chemistry, Stereoselective Synthesis, Atta-ur-Rahman, ed. Elsevier: Amsterdam, 1996, Vol. 18, p. 193; Zafra-Polo, M.C., Gonzalez, M.C., Estornell, E., Sahpaz, S., Cortes, D. Phytochemistry 1996, 42, 253.
7. Trost, B.M., Calkins, T.L., Bochet, C.G. Angew. Chem. Int. Ed. Engl. 1997, 36, 2632.
8. Koert, U., Stein, M., Wagner, H. Chem. Eur. J. 1997, 3, 1170.
9. 2 symmetric oligo-THFs (tetra- and penta-THFs).
10. Marshall, J.A., Hinkle, K.W. J. Org. Chem. 1996, 61, 4247.
11. Marshall, J.A., Hinkle, K.W. J. Org. Chem. 1997, 62, 5989.
12. Marshall, J.A., Chen, M. J. Org. Chem. 1997, 62, 5996.
13. Hoye, T.R., Ye, Z. J. Am. Chem. Soc. 1996, 118, 1801.
14. Wöhrle, I., Classen, A., Peterek, M., Scharf, H.-D. Tetrahedron Lett. 1996, 37, 7001.
15. Towne, T.B., McDonald, F.E. J. Am. Chem. Soc. 1997, 119, 6022.
16. Sinha, S.C., Sinha, A., Sinha, S.C., Keinan, E. J. Am. Chem. Soc. 1997, 119, 12014.
17. Suitable conformational models for syn-oxidative cyclizations have been proposed. See ref. 11.
18. For leading references on this subject, see: Maehr, H. Bioorg. Med. Chem. Lett. 1997, 5, 473; Still, W.C. Acc. Chem. Res. 1996, 29, 155; Thompson, L.A., Ellman, J.A. Chem. Rev. 1996, 96, 555, and references cited therein.
19. For leading references on this subject, see: Maehr, H. Bioorg. Med. Chem. Lett. 1997, 5, 473; Still, W.C. Acc. Chem. Res. 1996, 29, 155; Thompson, L.A., Ellman, J.A. Chem. Rev. 1996, 96, 555, and references cited therein.
20. For leading references on this subject, see: Maehr, H. Bioorg. Med. Chem. Lett. 1997, 5, 473; Still, W.C. Acc. Chem. Res. 1996, 29, 155; Thompson, L.A., Ellman, J.A. Chem. Rev. 1996, 96, 555, and references cited therein.
21. Sinha, S.C., Sinha, A., Yazbak, A., Keinan, E. J. Org. Chem. 1996, 61, 7640.
22. Keinan, E., Sinha, A., Yazbak, A., Sinha, S.C., Sinha, S.C. Pure Appl. Chem. 1997, 69, 423.
23. Figadère, B., Peyrat, J.-F., Cavé, A. J. Org. Chem. 1997, 62, 3428.
24. Zanardi, F., Battistini, L., Rassu, G., Pinna, L., Mor, M., Culeddu, N., Casiraghi, G. J. Org. Chem. 1998, 63, 1368.
25. A closely related approach was recently exploited by Hanessian during the total synthesis of an annonacin A-type acetogenin. Hanessian, S., Abad Grillo, T. J. Org. Chem. 1998, 63, 1049.
26. For comprehensive accounts on the use of oxygen, sulfur, and nitrogen-based silyloxy dienes, see: Casiraghi, G., Rassu, G. Synthesis 1995, 607; Casiraghi, G., Rassu, G., Zanardi, F. In Carbohydrate Mimics: Concepts and Methods, Chapleur, Y., ed. Wiley-VCH: Weinheim, 1998, Chap. 17, p. 327; Casiraghi, G., Rassu, G., Zanardi, F., Battistini, L. In Advances in Asymmetric Synthesis, Hassner, A., ed. JAI Press: Greenwich, Vol. 3, in press.
27. For comprehensive accounts on the use of oxygen, sulfur, and nitrogen-based silyloxy dienes, see: Casiraghi, G., Rassu, G. Synthesis 1995, 607; Casiraghi, G., Rassu, G., Zanardi, F. In Carbohydrate Mimics: Concepts and Methods, Chapleur, Y., ed. Wiley-VCH: Weinheim, 1998, Chap. 17, p. 327; Casiraghi, G., Rassu, G., Zanardi, F., Battistini, L. In Advances in Asymmetric Synthesis, Hassner, A., ed. JAI Press: Greenwich, Vol. 3, in press.
28. For comprehensive accounts on the use of oxygen, sulfur, and nitrogen-based silyloxy dienes, see: Casiraghi, G., Rassu, G. Synthesis 1995, 607; Casiraghi, G., Rassu, G., Zanardi, F. In Carbohydrate Mimics: Concepts and Methods, Chapleur, Y., ed. Wiley-VCH: Weinheim, 1998, Chap. 17, p. 327; Casiraghi, G., Rassu, G., Zanardi, F., Battistini, L. In Advances in Asymmetric Synthesis, Hassner, A., ed. JAI Press: Greenwich, Vol. 3, in press.
29. 2 symmetric trans,threo,trans,threo,trans terpyrrolidine unit was recently reported. See: Arndt, H.-D., Polborn, K., Koert, U. Tetrahedron Lett. 1997, 38, 3879.
30. Duret, P., Figadère, B., Hocquemiller, R., Cave, A. Tetrahedron Lett. 1997, 38, 8849.
31. Hoye, T.R., Lushi, T. U.S. Patent, US 5587491, Dec. 24, 1996, 24 pp; Chem. Abs. 1997, 126, 117859y.