Stereocontrolled total synthesis of an annonacin A-type acetogenin: Pseudoannonacin A?

Journal of Organic Chemistry

Volumn 63, Issue 4, 1998, Pages 1049-1057

  Hanessian, Stephen ^a   Grillo, Teresa Abad ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOGENIN; ANNONACIN; PSEUDOANNONACIN A; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; DIASTEREOISOMER; HYDROGENATION; OPTICAL ROTATION; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0032548960     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9713621     Document Type: Article

References (36)

1. For reviews, see: Rupprecht, Y. K.; Hui, J.-H.; McLaughlin, J. L. J. Nat. Prod. 1990, 53, 237. Fang, X.-P.; Rieser, M. J.; Gu, Z.-M.; Zhao, G.-X.; McLaughlin, J. L. Phytochem. Anal. 1993, 4, 27. Zeng L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 275. Cavé, A.; Frigadère, B.; Laurens, A.; Cortes, D. In Progress in the Chemistry of Organic Natural Products: Acetogenins From Annonaceae; Herz, W., Ed.; Springer-Verlag: New York, 1997; Vol. 70, pp 81-288.
2. For reviews, see: Rupprecht, Y. K.; Hui, J.-H.; McLaughlin, J. L. J. Nat. Prod. 1990, 53, 237. Fang, X.-P.; Rieser, M. J.; Gu, Z.-M.; Zhao, G.-X.; McLaughlin, J. L. Phytochem. Anal. 1993, 4, 27. Zeng L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 275. Cavé, A.; Frigadère, B.; Laurens, A.; Cortes, D. In Progress in the Chemistry of Organic Natural Products: Acetogenins From Annonaceae; Herz, W., Ed.; Springer-Verlag: New York, 1997; Vol. 70, pp 81-288.
3. For reviews, see: Rupprecht, Y. K.; Hui, J.-H.; McLaughlin, J. L. J. Nat. Prod. 1990, 53, 237. Fang, X.-P.; Rieser, M. J.; Gu, Z.-M.; Zhao, G.-X.; McLaughlin, J. L. Phytochem. Anal. 1993, 4, 27. Zeng L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 275. Cavé, A.; Frigadère, B.; Laurens, A.; Cortes, D. In Progress in the Chemistry of Organic Natural Products: Acetogenins From Annonaceae; Herz, W., Ed.; Springer-Verlag: New York, 1997; Vol. 70, pp 81-288.
4. For reviews, see: Rupprecht, Y. K.; Hui, J.-H.; McLaughlin, J. L. J. Nat. Prod. 1990, 53, 237. Fang, X.-P.; Rieser, M. J.; Gu, Z.-M.; Zhao, G.-X.; McLaughlin, J. L. Phytochem. Anal. 1993, 4, 27. Zeng L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 275. Cavé, A.; Frigadère, B.; Laurens, A.; Cortes, D. In Progress in the Chemistry of Organic Natural Products: Acetogenins From Annonaceae; Herz, W., Ed.; Springer-Verlag: New York, 1997; Vol. 70, pp 81-288.
5. McLaughlin, J.-L.; Chang, C.; Smith, D. L. In Human Medicinal Agents from Plants; Kinghorn, A. D., Baladrin, M. F., Eds.; American Chemical Society: Washington, DC, 1993; Chapter 9, p 117.
6. For recent reviews, see: Hoppe, R.; Scharf, H. D. Synthesis 1995, 1447. Frigadère, B. Acc. Chem. Res. 1995, 28, 359. For recent syntheses of bis-tetrahydrofuran types, see: Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1997, 62, 5989. Marshall, J. A.; Chen, M. J. Org. Chem. 1997, 62, 5996 and references therein.
7. For recent reviews, see: Hoppe, R.; Scharf, H. D. Synthesis 1995, 1447. Frigadère, B. Acc. Chem. Res. 1995, 28, 359. For recent syntheses of bis-tetrahydrofuran types, see: Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1997, 62, 5989. Marshall, J. A.; Chen, M. J. Org. Chem. 1997, 62, 5996 and references therein.
8. For recent reviews, see: Hoppe, R.; Scharf, H. D. Synthesis 1995, 1447. Frigadère, B. Acc. Chem. Res. 1995, 28, 359. For recent syntheses of bis-tetrahydrofuran types, see: Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1997, 62, 5989. Marshall, J. A.; Chen, M. J. Org. Chem. 1997, 62, 5996 and references therein.
9. For recent reviews, see: Hoppe, R.; Scharf, H. D. Synthesis 1995, 1447. Frigadère, B. Acc. Chem. Res. 1995, 28, 359. For recent syntheses of bis-tetrahydrofuran types, see: Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1997, 62, 5989. Marshall, J. A.; Chen, M. J. Org. Chem. 1997, 62, 5996 and references therein.
10. Trost, B. M.; Shi, Z. J. Am. Chem. Soc. 1994, 116, 7459.
11. Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1993, 115, 4891.
12. Makabe, H.; Tanaka, A. J.; Oritani, T. Chem. Soc., Perkin Trans. 1 1994, 1975.
13. Yao, Z.-J.; Wu, Y.-L. J. Org. Chem. 1995, 60, 1170.
14. Harmange, J.-C.; Cavé, A.; Figadère, B. Tetrahedron Lett. 1992, 33, 5749.
15. Hoppe, R.; Flasche, M.; Scharf, H.-D. Tetrahedron Lett. 1994, 35, 2873.
16. Lieb, F.; Nonfon, M.; Wachendorff-Neumann, U.; Wendisch, D. Planta Med. 1990, 56, 317.
17. Compare for example the representations of annonacin A and related analogues in refs 4-9.
18. Hanessian, S.; Murray, P. J. Tetrahedron 1987, 43, 5055.
19. (a) Jefford, C. W.; Jaggi, D.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4037.
20. (b) Rassu, G.; Spanu, P.; Casiraghi, G.; Pinna, L. Tetrahedron 1991, 47, 8025 and the references therein.
21. Koert, U.; Stein, M.; Harms, K. Tetrahedron Lett. 1993, 34, 2299. See also: Frigadère, B.; Chaboche, C.; Peyrat, J.-F.; Cavé, A. Tetrahedron Lett. 1993, 34, 8093. Frigadère, B.; Peyrat, J.-F.; Cavé, A. J. Org. Chem. 1997, 62, 3428.
22. Koert, U.; Stein, M.; Harms, K. Tetrahedron Lett. 1993, 34, 2299. See also: Frigadère, B.; Chaboche, C.; Peyrat, J.-F.; Cavé, A. Tetrahedron Lett. 1993, 34, 8093. Frigadère, B.; Peyrat, J.-F.; Cavé, A. J. Org. Chem. 1997, 62, 3428.
23. Koert, U.; Stein, M.; Harms, K. Tetrahedron Lett. 1993, 34, 2299. See also: Frigadère, B.; Chaboche, C.; Peyrat, J.-F.; Cavé, A. Tetrahedron Lett. 1993, 34, 8093. Frigadère, B.; Peyrat, J.-F.; Cavé, A. J. Org. Chem. 1997, 62, 3428.
24. See, for example: (a) Hanessian, S.; Faucher, A.-M. J. Org. Chem. 1991, 56, 2947. (b) Melillo, D. G.; Liu, T.; Ryan, K.; Sletzinger, M.; Shinkai, I. Tetrahedron Lett. 1981, 22, 913. (c) Hughes, D. L. In Organic Reactions; Paquette, L. A.; et al., Eds.; Wiley: New York, 1992; Vol. 42, Chapter 2. (d) Mitsunobu, O. Synthesis 1981, 1.
25. See, for example: (a) Hanessian, S.; Faucher, A.-M. J. Org. Chem. 1991, 56, 2947. (b) Melillo, D. G.; Liu, T.; Ryan, K.; Sletzinger, M.; Shinkai, I. Tetrahedron Lett. 1981, 22, 913. (c) Hughes, D. L. In Organic Reactions; Paquette, L. A.; et al., Eds.; Wiley: New York, 1992; Vol. 42, Chapter 2. (d) Mitsunobu, O. Synthesis 1981, 1.
26. See, for example: (a) Hanessian, S.; Faucher, A.-M. J. Org. Chem. 1991, 56, 2947. (b) Melillo, D. G.; Liu, T.; Ryan, K.; Sletzinger, M.; Shinkai, I. Tetrahedron Lett. 1981, 22, 913. (c) Hughes, D. L. In Organic Reactions; Paquette, L. A.; et al., Eds.; Wiley: New York, 1992; Vol. 42, Chapter 2. (d) Mitsunobu, O. Synthesis 1981, 1.
27. See, for example: (a) Hanessian, S.; Faucher, A.-M. J. Org. Chem. 1991, 56, 2947. (b) Melillo, D. G.; Liu, T.; Ryan, K.; Sletzinger, M.; Shinkai, I. Tetrahedron Lett. 1981, 22, 913. (c) Hughes, D. L. In Organic Reactions; Paquette, L. A.; et al., Eds.; Wiley: New York, 1992; Vol. 42, Chapter 2. (d) Mitsunobu, O. Synthesis 1981, 1.
28. Buchanan, J. G.; Edgar, A. R.; Power, M. J.; Theaker, P. D. Carbohydr. Res. 1974, 38, C22.
29. Griffith, W. P.; Ley, S. V. Aldrichimica Acta 1990, 23, 13.
30. Frigadère, B.; Harmange, J.-C.; Laurens, A.; Cavé, A. Tetrahedron Lett. 1991, 32, 7539.
31. Wolfrom, M. L.; Hanessian, S. J. Org. Chem. 1962, 27, 1800.
32. See, for example: Bartlett, P. A.; Green, F. R.; Rose, E. H. J. Am. Chem. Soc. 1978, 100, 4852.
33. Kocienski, P. J.; Lythgoe, B.; Ruston, S. J. Chem. Soc., Perkin Trans. 1 1978, 829.
34. Naito, H.; Kawahara, E.; Maruta, K.; Maeda, M.; Sasaki, S. J. Org. Chem. 1995, 60, 4419.
35. Hanessian, S.; Delorme, D.; Dufresne, Y. Tetrahedron Lett. 1984, 25, 2515.
36. For the determination of absolute configuration of certain acetogenins, see: Rieser, M. J.; Hui, Y.-H.; Rupprecht, K.; Kozlowski, J. F. Wood, K. V.; McLaughlin, J. L.; Hanson, P. R.; Zhuang, Z.; Hoye, T. R. J. Am. Chem. Soc. 1992, 114, 10203.