The utility of furan-, pyrrole-, and thiophene-based 2-silyloxy dienes as demonstrated by modular synthesis of annonaceous acetogenin core units and their pyrrolidine and thiolane analogues

Journal of Organic Chemistry

Volumn 65, Issue 7, 2000, Pages 2048-2064

  Zanardi, Franca ^a   Battistini, Lucia ^a   Rassu, Gloria ^b   Auzzas, Luciana ^b   Pinna, Luigi ^c   Marzocchi, Lucia ^a   Acquotti, Domenico ^a   Casiraghi, Giovanni ^a  

^a UNIVERSITY OF PARMA   (Italy)

^b CNR   (Italy)

^c UNIVERSITY OF SASSARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOGENIN; FURAN; FURAN DERIVATIVE; NITROGEN DERIVATIVE; PYRROLE; PYRROLE DERIVATIVE; PYRROLIDINE DERIVATIVE; SULFUR DERIVATIVE; THIOLANE; THIOPHENE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; ENERGY TRANSFER; SYNTHESIS;

FURANS; PLANTS, MEDICINAL; PYRROLES; THIOPHENES;

EID: 0034616281     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991568x     Document Type: Article

References (44)

1. For recent comprehensive reviews, see: Alali, F. Q.; Liu, X.-X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504-540. Cavé, A.; Figadère, B.; Laurens, A.; Cortes, D. In Progress in the Chemistry of Organic Natural Products; Herz, W., Ed.; Springer-Verlag: Wien, New York, 1997; Vol. 70, pp 81-288. Gu, Z.-M.; Zhao, G.-X.; Oberlies, N. H.; Zeng, L.; McLaughlin, J. L. In Recent Advances in Phytochemistry; Arnason, J. T., Mata, R., Romeo, J. T., Eds.; Plenum Press: New York, 1995; Vol. 29, Chapter 11, pp 249-310. Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 275-306. Cavé, A.; Cortes, D.; Figadère, B.; Hocquemiller, R.; Laprévote, O.; Laurens, A.; Lebœuf, M. In Phytochemical Potential of Tropical Plants; Downum, K. R., Romeo, J. T., Stafford, H. E., Eds.; Plenum Press: New York, 1993; pp 167-202. Marshall, J. A.; Hinkle, K. W.; Hagedorn, C. E. Recent Developments in the Synthesis of Annonaceous Acetogenins. Isr. J. Chem. 1997, 37, 97-107. Zafra-Polo, M. C.; Figadère, B.; Gallardo, T.; Tormo, J. R.; Cortes, D. Phytochemistry 1998, 48, 1087-1117. Casiraghi, G.; Zanardi, F.; Battistini, L.; Rassu, G.; Appendino, G. Chemtracts Org. Chem. 1998, 11, 803-827 and references therein.
2. For recent comprehensive reviews, see: Alali, F. Q.; Liu, X.-X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504-540. Cavé, A.; Figadère, B.; Laurens, A.; Cortes, D. In Progress in the Chemistry of Organic Natural Products; Herz, W., Ed.; Springer-Verlag: Wien, New York, 1997; Vol. 70, pp 81-288. Gu, Z.-M.; Zhao, G.-X.; Oberlies, N. H.; Zeng, L.; McLaughlin, J. L. In Recent Advances in Phytochemistry; Arnason, J. T., Mata, R., Romeo, J. T., Eds.; Plenum Press: New York, 1995; Vol. 29, Chapter 11, pp 249-310. Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 275-306. Cavé, A.; Cortes, D.; Figadère, B.; Hocquemiller, R.; Laprévote, O.; Laurens, A.; Lebœuf, M. In Phytochemical Potential of Tropical Plants; Downum, K. R., Romeo, J. T., Stafford, H. E., Eds.; Plenum Press: New York, 1993; pp 167-202. Marshall, J. A.; Hinkle, K. W.; Hagedorn, C. E. Recent Developments in the Synthesis of Annonaceous Acetogenins. Isr. J. Chem. 1997, 37, 97-107. Zafra-Polo, M. C.; Figadère, B.; Gallardo, T.; Tormo, J. R.; Cortes, D. Phytochemistry 1998, 48, 1087-1117. Casiraghi, G.; Zanardi, F.; Battistini, L.; Rassu, G.; Appendino, G. Chemtracts Org. Chem. 1998, 11, 803-827 and references therein.
3. For recent comprehensive reviews, see: Alali, F. Q.; Liu, X.-X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504-540. Cavé, A.; Figadère, B.; Laurens, A.; Cortes, D. In Progress in the Chemistry of Organic Natural Products; Herz, W., Ed.; Springer-Verlag: Wien, New York, 1997; Vol. 70, pp 81-288. Gu, Z.-M.; Zhao, G.-X.; Oberlies, N. H.; Zeng, L.; McLaughlin, J. L. In Recent Advances in Phytochemistry; Arnason, J. T., Mata, R., Romeo, J. T., Eds.; Plenum Press: New York, 1995; Vol. 29, Chapter 11, pp 249-310. Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 275-306. Cavé, A.; Cortes, D.; Figadère, B.; Hocquemiller, R.; Laprévote, O.; Laurens, A.; Lebœuf, M. In Phytochemical Potential of Tropical Plants; Downum, K. R., Romeo, J. T., Stafford, H. E., Eds.; Plenum Press: New York, 1993; pp 167-202. Marshall, J. A.; Hinkle, K. W.; Hagedorn, C. E. Recent Developments in the Synthesis of Annonaceous Acetogenins. Isr. J. Chem. 1997, 37, 97-107. Zafra-Polo, M. C.; Figadère, B.; Gallardo, T.; Tormo, J. R.; Cortes, D. Phytochemistry 1998, 48, 1087-1117. Casiraghi, G.; Zanardi, F.; Battistini, L.; Rassu, G.; Appendino, G. Chemtracts Org. Chem. 1998, 11, 803-827 and references therein.
4. For recent comprehensive reviews, see: Alali, F. Q.; Liu, X.-X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504-540. Cavé, A.; Figadère, B.; Laurens, A.; Cortes, D. In Progress in the Chemistry of Organic Natural Products; Herz, W., Ed.; Springer-Verlag: Wien, New York, 1997; Vol. 70, pp 81-288. Gu, Z.-M.; Zhao, G.-X.; Oberlies, N. H.; Zeng, L.; McLaughlin, J. L. In Recent Advances in Phytochemistry; Arnason, J. T., Mata, R., Romeo, J. T., Eds.; Plenum Press: New York, 1995; Vol. 29, Chapter 11, pp 249-310. Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 275-306. Cavé, A.; Cortes, D.; Figadère, B.; Hocquemiller, R.; Laprévote, O.; Laurens, A.; Lebœuf, M. In Phytochemical Potential of Tropical Plants; Downum, K. R., Romeo, J. T., Stafford, H. E., Eds.; Plenum Press: New York, 1993; pp 167-202. Marshall, J. A.; Hinkle, K. W.; Hagedorn, C. E. Recent Developments in the Synthesis of Annonaceous Acetogenins. Isr. J. Chem. 1997, 37, 97-107. Zafra-Polo, M. C.; Figadère, B.; Gallardo, T.; Tormo, J. R.; Cortes, D. Phytochemistry 1998, 48, 1087-1117. Casiraghi, G.; Zanardi, F.; Battistini, L.; Rassu, G.; Appendino, G. Chemtracts Org. Chem. 1998, 11, 803-827 and references therein.
5. For recent comprehensive reviews, see: Alali, F. Q.; Liu, X.-X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504-540. Cavé, A.; Figadère, B.; Laurens, A.; Cortes, D. In Progress in the Chemistry of Organic Natural Products; Herz, W., Ed.; Springer-Verlag: Wien, New York, 1997; Vol. 70, pp 81-288. Gu, Z.-M.; Zhao, G.-X.; Oberlies, N. H.; Zeng, L.; McLaughlin, J. L. In Recent Advances in Phytochemistry; Arnason, J. T., Mata, R., Romeo, J. T., Eds.; Plenum Press: New York, 1995; Vol. 29, Chapter 11, pp 249-310. Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 275-306. Cavé, A.; Cortes, D.; Figadère, B.; Hocquemiller, R.; Laprévote, O.; Laurens, A.; Lebœuf, M. In Phytochemical Potential of Tropical Plants; Downum, K. R., Romeo, J. T., Stafford, H. E., Eds.; Plenum Press: New York, 1993; pp 167-202. Marshall, J. A.; Hinkle, K. W.; Hagedorn, C. E. Recent Developments in the Synthesis of Annonaceous Acetogenins. Isr. J. Chem. 1997, 37, 97-107. Zafra-Polo, M. C.; Figadère, B.; Gallardo, T.; Tormo, J. R.; Cortes, D. Phytochemistry 1998, 48, 1087-1117. Casiraghi, G.; Zanardi, F.; Battistini, L.; Rassu, G.; Appendino, G. Chemtracts Org. Chem. 1998, 11, 803-827 and references therein.
6. For recent comprehensive reviews, see: Alali, F. Q.; Liu, X.-X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504-540. Cavé, A.; Figadère, B.; Laurens, A.; Cortes, D. In Progress in the Chemistry of Organic Natural Products; Herz, W., Ed.; Springer-Verlag: Wien, New York, 1997; Vol. 70, pp 81-288. Gu, Z.-M.; Zhao, G.-X.; Oberlies, N. H.; Zeng, L.; McLaughlin, J. L. In Recent Advances in Phytochemistry; Arnason, J. T., Mata, R., Romeo, J. T., Eds.; Plenum Press: New York, 1995; Vol. 29, Chapter 11, pp 249-310. Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 275-306. Cavé, A.; Cortes, D.; Figadère, B.; Hocquemiller, R.; Laprévote, O.; Laurens, A.; Lebœuf, M. In Phytochemical Potential of Tropical Plants; Downum, K. R., Romeo, J. T., Stafford, H. E., Eds.; Plenum Press: New York, 1993; pp 167-202. Marshall, J. A.; Hinkle, K. W.; Hagedorn, C. E. Recent Developments in the Synthesis of Annonaceous Acetogenins. Isr. J. Chem. 1997, 37, 97-107. Zafra-Polo, M. C.; Figadère, B.; Gallardo, T.; Tormo, J. R.; Cortes, D. Phytochemistry 1998, 48, 1087-1117. Casiraghi, G.; Zanardi, F.; Battistini, L.; Rassu, G.; Appendino, G. Chemtracts Org. Chem. 1998, 11, 803-827 and references therein.
7. For recent comprehensive reviews, see: Alali, F. Q.; Liu, X.-X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504-540. Cavé, A.; Figadère, B.; Laurens, A.; Cortes, D. In Progress in the Chemistry of Organic Natural Products; Herz, W., Ed.; Springer-Verlag: Wien, New York, 1997; Vol. 70, pp 81-288. Gu, Z.-M.; Zhao, G.-X.; Oberlies, N. H.; Zeng, L.; McLaughlin, J. L. In Recent Advances in Phytochemistry; Arnason, J. T., Mata, R., Romeo, J. T., Eds.; Plenum Press: New York, 1995; Vol. 29, Chapter 11, pp 249-310. Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 275-306. Cavé, A.; Cortes, D.; Figadère, B.; Hocquemiller, R.; Laprévote, O.; Laurens, A.; Lebœuf, M. In Phytochemical Potential of Tropical Plants; Downum, K. R., Romeo, J. T., Stafford, H. E., Eds.; Plenum Press: New York, 1993; pp 167-202. Marshall, J. A.; Hinkle, K. W.; Hagedorn, C. E. Recent Developments in the Synthesis of Annonaceous Acetogenins. Isr. J. Chem. 1997, 37, 97-107. Zafra-Polo, M. C.; Figadère, B.; Gallardo, T.; Tormo, J. R.; Cortes, D. Phytochemistry 1998, 48, 1087-1117. Casiraghi, G.; Zanardi, F.; Battistini, L.; Rassu, G.; Appendino, G. Chemtracts Org. Chem. 1998, 11, 803-827 and references therein.
8. For recent comprehensive reviews, see: Alali, F. Q.; Liu, X.-X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504-540. Cavé, A.; Figadère, B.; Laurens, A.; Cortes, D. In Progress in the Chemistry of Organic Natural Products; Herz, W., Ed.; Springer-Verlag: Wien, New York, 1997; Vol. 70, pp 81-288. Gu, Z.-M.; Zhao, G.-X.; Oberlies, N. H.; Zeng, L.; McLaughlin, J. L. In Recent Advances in Phytochemistry; Arnason, J. T., Mata, R., Romeo, J. T., Eds.; Plenum Press: New York, 1995; Vol. 29, Chapter 11, pp 249-310. Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 275-306. Cavé, A.; Cortes, D.; Figadère, B.; Hocquemiller, R.; Laprévote, O.; Laurens, A.; Lebœuf, M. In Phytochemical Potential of Tropical Plants; Downum, K. R., Romeo, J. T., Stafford, H. E., Eds.; Plenum Press: New York, 1993; pp 167-202. Marshall, J. A.; Hinkle, K. W.; Hagedorn, C. E. Recent Developments in the Synthesis of Annonaceous Acetogenins. Isr. J. Chem. 1997, 37, 97-107. Zafra-Polo, M. C.; Figadère, B.; Gallardo, T.; Tormo, J. R.; Cortes, D. Phytochemistry 1998, 48, 1087-1117. Casiraghi, G.; Zanardi, F.; Battistini, L.; Rassu, G.; Appendino, G. Chemtracts Org. Chem. 1998, 11, 803-827 and references therein.
9. Jolad, S. D.; Hoffmann, J. J.; Schram, K. H.; Cole, J. R.; Tempesta, M. S.; Kriek, G. R.; Bates, R. B. J. Org. Chem. 1982, 47, 3151-3153.
10. Recently, a few tetrahydropyran-containing analogues have been isolated and synthesized: Schaus, S.; Brånalt, J.; Jacobsen, E. J. Org. Chem. 1998, 63, 4876-4877. Neogi, P.; Doundoulakis, T.; Yazbak, A.; Sinha, S. C.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1998, 120, 11279-11284. Takahashi, S.; Nakata, T. Tetrahedron Lett. 1999, 40, 723-726. Evans, P. A.; Murthy, V. S. Tetrahedron Lett. 1999, 40, 1253-1256.
11. Recently, a few tetrahydropyran-containing analogues have been isolated and synthesized: Schaus, S.; Brånalt, J.; Jacobsen, E. J. Org. Chem. 1998, 63, 4876-4877. Neogi, P.; Doundoulakis, T.; Yazbak, A.; Sinha, S. C.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1998, 120, 11279-11284. Takahashi, S.; Nakata, T. Tetrahedron Lett. 1999, 40, 723-726. Evans, P. A.; Murthy, V. S. Tetrahedron Lett. 1999, 40, 1253-1256.
12. Recently, a few tetrahydropyran-containing analogues have been isolated and synthesized: Schaus, S.; Brånalt, J.; Jacobsen, E. J. Org. Chem. 1998, 63, 4876-4877. Neogi, P.; Doundoulakis, T.; Yazbak, A.; Sinha, S. C.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1998, 120, 11279-11284. Takahashi, S.; Nakata, T. Tetrahedron Lett. 1999, 40, 723-726. Evans, P. A.; Murthy, V. S. Tetrahedron Lett. 1999, 40, 1253-1256.
13. Recently, a few tetrahydropyran-containing analogues have been isolated and synthesized: Schaus, S.; Brånalt, J.; Jacobsen, E. J. Org. Chem. 1998, 63, 4876-4877. Neogi, P.; Doundoulakis, T.; Yazbak, A.; Sinha, S. C.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1998, 120, 11279-11284. Takahashi, S.; Nakata, T. Tetrahedron Lett. 1999, 40, 723-726. Evans, P. A.; Murthy, V. S. Tetrahedron Lett. 1999, 40, 1253-1256.
14. Holschneider, C. H.; Johnson, M. T.; Knox, R. M.; Rezai, A.; Ryan, W. J.; Montz, F. J. Cancer Chemother. Pharmacol. 1994, 34, 166-170. Degli Esposti, M.; Ghelli, A.; Ratta, M.; Cortes, D.; Estornell, E. Biochem. J. 1994, 301, 161-167. Oberlies, N. H.; Jones, J. L.; Corbett, T. H.; Fotopoulos, S. S.; McLaughlin, J. L. Cancer Lett. 1995, 96, 55- 62. Morré, D. J.; de Cabo, R.; Farley, C.; Oberlies, N. H.; McLaughlin, J. L. Life Sci. 1995, 56, 343-348 . Oberlies, N. H.; Croy, V. L.; Harrison, M. L.; McLaughlin, J. L. Cancer Lett. 1997, 115, 73-79. Wang, X.-W.; Xie, H. Drugs Future 1999, 24, 159-165.
15. Holschneider, C. H.; Johnson, M. T.; Knox, R. M.; Rezai, A.; Ryan, W. J.; Montz, F. J. Cancer Chemother. Pharmacol. 1994, 34, 166-170. Degli Esposti, M.; Ghelli, A.; Ratta, M.; Cortes, D.; Estornell, E. Biochem. J. 1994, 301, 161-167. Oberlies, N. H.; Jones, J. L.; Corbett, T. H.; Fotopoulos, S. S.; McLaughlin, J. L. Cancer Lett. 1995, 96, 55- 62. Morré, D. J.; de Cabo, R.; Farley, C.; Oberlies, N. H.; McLaughlin, J. L. Life Sci. 1995, 56, 343-348 . Oberlies, N. H.; Croy, V. L.; Harrison, M. L.; McLaughlin, J. L. Cancer Lett. 1997, 115, 73-79. Wang, X.-W.; Xie, H. Drugs Future 1999, 24, 159-165.
16. Holschneider, C. H.; Johnson, M. T.; Knox, R. M.; Rezai, A.; Ryan, W. J.; Montz, F. J. Cancer Chemother. Pharmacol. 1994, 34, 166-170. Degli Esposti, M.; Ghelli, A.; Ratta, M.; Cortes, D.; Estornell, E. Biochem. J. 1994, 301, 161-167. Oberlies, N. H.; Jones, J. L.; Corbett, T. H.; Fotopoulos, S. S.; McLaughlin, J. L. Cancer Lett. 1995, 96, 55-62. Morré, D. J.; de Cabo, R.; Farley, C.; Oberlies, N. H.; McLaughlin, J. L. Life Sci. 1995, 56, 343-348 . Oberlies, N. H.; Croy, V. L.; Harrison, M. L.; McLaughlin, J. L. Cancer Lett. 1997, 115, 73-79. Wang, X.-W.; Xie, H. Drugs Future 1999, 24, 159-165.
17. Holschneider, C. H.; Johnson, M. T.; Knox, R. M.; Rezai, A.; Ryan, W. J.; Montz, F. J. Cancer Chemother. Pharmacol. 1994, 34, 166-170. Degli Esposti, M.; Ghelli, A.; Ratta, M.; Cortes, D.; Estornell, E. Biochem. J. 1994, 301, 161-167. Oberlies, N. H.; Jones, J. L.; Corbett, T. H.; Fotopoulos, S. S.; McLaughlin, J. L. Cancer Lett. 1995, 96, 55- 62. Morré, D. J.; de Cabo, R.; Farley, C.; Oberlies, N. H.; McLaughlin, J. L. Life Sci. 1995, 56, 343-348 . Oberlies, N. H.; Croy, V. L.; Harrison, M. L.; McLaughlin, J. L. Cancer Lett. 1997, 115, 73-79. Wang, X.-W.; Xie, H. Drugs Future 1999, 24, 159-165.
18. Holschneider, C. H.; Johnson, M. T.; Knox, R. M.; Rezai, A.; Ryan, W. J.; Montz, F. J. Cancer Chemother. Pharmacol. 1994, 34, 166-170. Degli Esposti, M.; Ghelli, A.; Ratta, M.; Cortes, D.; Estornell, E. Biochem. J. 1994, 301, 161-167. Oberlies, N. H.; Jones, J. L.; Corbett, T. H.; Fotopoulos, S. S.; McLaughlin, J. L. Cancer Lett. 1995, 96, 55- 62. Morré, D. J.; de Cabo, R.; Farley, C.; Oberlies, N. H.; McLaughlin, J. L. Life Sci. 1995, 56, 343-348 . Oberlies, N. H.; Croy, V. L.; Harrison, M. L.; McLaughlin, J. L. Cancer Lett. 1997, 115, 73-79. Wang, X.-W.; Xie, H. Drugs Future 1999, 24, 159-165.
19. Holschneider, C. H.; Johnson, M. T.; Knox, R. M.; Rezai, A.; Ryan, W. J.; Montz, F. J. Cancer Chemother. Pharmacol. 1994, 34, 166-170. Degli Esposti, M.; Ghelli, A.; Ratta, M.; Cortes, D.; Estornell, E. Biochem. J. 1994, 301, 161-167. Oberlies, N. H.; Jones, J. L.; Corbett, T. H.; Fotopoulos, S. S.; McLaughlin, J. L. Cancer Lett. 1995, 96, 55- 62. Morré, D. J.; de Cabo, R.; Farley, C.; Oberlies, N. H.; McLaughlin, J. L. Life Sci. 1995, 56, 343-348 . Oberlies, N. H.; Croy, V. L.; Harrison, M. L.; McLaughlin, J. L. Cancer Lett. 1997, 115, 73-79. Wang, X.-W.; Xie, H. Drugs Future 1999, 24, 159-165.
20. For general reviews: Casiraghi, G.; Rassu, G. Synthesis 1995, 607-629. Casiraghi, G.; Rassu, G.; Zanardi, F.; Battistini, L. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Stamford; 1998; Vol. 3, pp 113-189. Rassu, G.; Zanardi, F.; Battistini, L.; Casiraghi, G. Synlett 1999, 1333-1350.
21. For general reviews: Casiraghi, G.; Rassu, G. Synthesis 1995, 607-629. Casiraghi, G.; Rassu, G.; Zanardi, F.; Battistini, L. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Stamford; 1998; Vol. 3, pp 113-189. Rassu, G.; Zanardi, F.; Battistini, L.; Casiraghi, G. Synlett 1999, 1333-1350.
22. For general reviews: Casiraghi, G.; Rassu, G. Synthesis 1995, 607-629. Casiraghi, G.; Rassu, G.; Zanardi, F.; Battistini, L. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Stamford; 1998; Vol. 3, pp 113-189. Rassu, G.; Zanardi, F.; Battistini, L.; Casiraghi, G. Synlett 1999, 1333-1350.
23. For leading references concerning the reactivity of vinylogous carbon nucleophiles, see, for example: Christoffers, J. J. Org. Chem. 1998, 63, 4539-4540. Saito, S.; Shiozawa, M.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 813-814. Krüger, J.; Carreira, E. M. Tetrahedron Lett. 1998, 39, 7013-7016. Saito, S.; Yamamoto, H. Chem. Eur. J. 1999, 5, 1959-1962. Martin, S. F.; Lopez, O. D. Tetrahedron Lett. 1999, 40, 8949-8953. Hara, R.; Furukawa, T.; Kashima, H.; Kusama, H.; Horiguchi, Y.; Kuwajima, I. J. Am. Chem. Soc. 1999, 121, 3072-3082. Evans, D. A.; Ripin, D. H. B.; Halstead, D. P.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 6816-6826.
24. For leading references concerning the reactivity of vinylogous carbon nucleophiles, see, for example: Christoffers, J. J. Org. Chem. 1998, 63, 4539-4540. Saito, S.; Shiozawa, M.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 813-814. Krüger, J.; Carreira, E. M. Tetrahedron Lett. 1998, 39, 7013-7016. Saito, S.; Yamamoto, H. Chem. Eur. J. 1999, 5, 1959-1962. Martin, S. F.; Lopez, O. D. Tetrahedron Lett. 1999, 40, 8949-8953. Hara, R.; Furukawa, T.; Kashima, H.; Kusama, H.; Horiguchi, Y.; Kuwajima, I. J. Am. Chem. Soc. 1999, 121, 3072-3082. Evans, D. A.; Ripin, D. H. B.; Halstead, D. P.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 6816-6826.
25. For leading references concerning the reactivity of vinylogous carbon nucleophiles, see, for example: Christoffers, J. J. Org. Chem. 1998, 63, 4539-4540. Saito, S.; Shiozawa, M.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 813-814. Krüger, J.; Carreira, E. M. Tetrahedron Lett. 1998, 39, 7013-7016. Saito, S.; Yamamoto, H. Chem. Eur. J. 1999, 5, 1959-1962. Martin, S. F.; Lopez, O. D. Tetrahedron Lett. 1999, 40, 8949-8953. Hara, R.; Furukawa, T.; Kashima, H.; Kusama, H.; Horiguchi, Y.; Kuwajima, I. J. Am. Chem. Soc. 1999, 121, 3072-3082. Evans, D. A.; Ripin, D. H. B.; Halstead, D. P.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 6816-6826.
26. For leading references concerning the reactivity of vinylogous carbon nucleophiles, see, for example: Christoffers, J. J. Org. Chem. 1998, 63, 4539-4540. Saito, S.; Shiozawa, M.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 813-814. Krüger, J.; Carreira, E. M. Tetrahedron Lett. 1998, 39, 7013-7016. Saito, S.; Yamamoto, H. Chem. Eur. J. 1999, 5, 1959-1962. Martin, S. F.; Lopez, O. D. Tetrahedron Lett. 1999, 40, 8949-8953. Hara, R.; Furukawa, T.; Kashima, H.; Kusama, H.; Horiguchi, Y.; Kuwajima, I. J. Am. Chem. Soc. 1999, 121, 3072-3082. Evans, D. A.; Ripin, D. H. B.; Halstead, D. P.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 6816-6826.
27. For leading references concerning the reactivity of vinylogous carbon nucleophiles, see, for example: Christoffers, J. J. Org. Chem. 1998, 63, 4539-4540. Saito, S.; Shiozawa, M.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 813-814. Krüger, J.; Carreira, E. M. Tetrahedron Lett. 1998, 39, 7013-7016. Saito, S.; Yamamoto, H. Chem. Eur. J. 1999, 5, 1959-1962. Martin, S. F.; Lopez, O. D. Tetrahedron Lett. 1999, 40, 8949-8953. Hara, R.; Furukawa, T.; Kashima, H.; Kusama, H.; Horiguchi, Y.; Kuwajima, I. J. Am. Chem. Soc. 1999, 121, 3072-3082. Evans, D. A.; Ripin, D. H. B.; Halstead, D. P.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 6816-6826.
28. For leading references concerning the reactivity of vinylogous carbon nucleophiles, see, for example: Christoffers, J. J. Org. Chem. 1998, 63, 4539-4540. Saito, S.; Shiozawa, M.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 813-814. Krüger, J.; Carreira, E. M. Tetrahedron Lett. 1998, 39, 7013-7016. Saito, S.; Yamamoto, H. Chem. Eur. J. 1999, 5, 1959-1962. Martin, S. F.; Lopez, O. D. Tetrahedron Lett. 1999, 40, 8949-8953. Hara, R.; Furukawa, T.; Kashima, H.; Kusama, H.; Horiguchi, Y.; Kuwajima, I. J. Am. Chem. Soc. 1999, 121, 3072-3082. Evans, D. A.; Ripin, D. H. B.; Halstead, D. P.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 6816-6826.
29. For leading references concerning the reactivity of vinylogous carbon nucleophiles, see, for example: Christoffers, J. J. Org. Chem. 1998, 63, 4539-4540. Saito, S.; Shiozawa, M.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 813-814. Krüger, J.; Carreira, E. M. Tetrahedron Lett. 1998, 39, 7013-7016. Saito, S.; Yamamoto, H. Chem. Eur. J. 1999, 5, 1959-1962. Martin, S. F.; Lopez, O. D. Tetrahedron Lett. 1999, 40, 8949-8953. Hara, R.; Furukawa, T.; Kashima, H.; Kusama, H.; Horiguchi, Y.; Kuwajima, I. J. Am. Chem. Soc. 1999, 121, 3072-3082. Evans, D. A.; Ripin, D. H. B.; Halstead, D. P.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 6816-6826.
30. For a preliminary account of the work in this section, see: Zanardi, F.; Battistini, L.; Rassu, G.; Pinna, L.; Mor, M.; Culeddu, N.; Casiraghi, G. J. Org. Chem. 1998, 63, 1368-1369.
31. 2O, 4 Å molecular sieves) (52% yield over four steps).
32. The suffixes associated to conventional numbering in model compounds 4-21 relate to the relative stereodisposition of the C4-C5 and C5-C8 stereocenters: e.g., 4tt = 4,5-threo-5,8-trans-4; 14ec = 4,5-erythro-5,8-cis-14, etc.
33. Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P.; Gasparri Fava, G.; Ferrari Belicchi, M. Tetrahedron 1990, 46, 5807-5824.
34. Gawronski, J. K.; van Oeveren, A.; van der Deen, H.; Leung, C. W.; Feringa, B. L. J. Org. Chem. 1996, 61, 1513-1515. Cuiper, A. D.; Brzostowska, M.; Gawronski, J. K.; Smeets, W. J. J.; Spek, A. L.; Hiemstra, H.; Kellogg, R. M.; Feringa, B. L. J. Org. Chem. 1999, 64, 2567-2570.
35. Gawronski, J. K.; van Oeveren, A.; van der Deen, H.; Leung, C. W.; Feringa, B. L. J. Org. Chem. 1996, 61, 1513-1515. Cuiper, A. D.; Brzostowska, M.; Gawronski, J. K.; Smeets, W. J. J.; Spek, A. L.; Hiemstra, H.; Kellogg, R. M.; Feringa, B. L. J. Org. Chem. 1999, 64, 2567-2570.
36. For some representative binuclear fragments, a molecular mechanics calculation was performed, simulating a rotation around the C4-C5 bond. The calculation of the relative populations of anti and gauche conformations allowed the prediction of the mean J values, which were in good accordance with the experimental ones. See note 12 in ref 7.
37. Figadère, B.; Chaboche, C.; Peyrat, J.-F.; Cavé, A. Tetrahedron Lett. 1993, 34, 8093-8096. Jefford, C. W.; Jaggi, D.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4037-4040.
38. Figadère, B.; Chaboche, C.; Peyrat, J.-F.; Cavé, A. Tetrahedron Lett. 1993, 34, 8093-8096. Jefford, C. W.; Jaggi, D.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4037-4040.
39. Boeckman, R. K. Jr.; Potenza, J. C. Tetrahedron Lett. 1985, 26, 1411-1414.
40. In the preliminary account of this work (ref 7) the stereostructures of compounds 14ec and 14et were misassigned as threo,trans and threo,cis isomers, respectively.
41. 37 annonaceous acetogenin A in Scheme 1.
42. Although TBSOTf is actually a reagent for cleaving N-Boc linkages, no traces of N-deprotected compounds were found in this and similar instances.
43. Owing to the high diastereoselectivity observed in the model coupling reaction between TBSOF and N,O-acetal 2, favoring threo,trans-configured adduct 10tt, one can reason that a similar behavior is here followed, too. See also: Hanessian, S.; McNaughton-Smith, G. Bioorg. Med. Chem. Lett. 1996, 6, 1567-1572. Martin, S. F.; Barr, K. J.; Smith, D. W.; Bur, S. K. J. Am. Chem. Soc. 1999, 121, 6990-6997.
44. Owing to the high diastereoselectivity observed in the model coupling reaction between TBSOF and N,O-acetal 2, favoring threo,trans-configured adduct 10tt, one can reason that a similar behavior is here followed, too. See also: Hanessian, S.; McNaughton- Smith, G. Bioorg. Med. Chem. Lett. 1996, 6, 1567-1572. Martin, S. F.; Barr, K. J.; Smith, D. W.; Bur, S. K. J. Am. Chem. Soc. 1999, 121, 6990-6997.