Systematic synthesis of bis-THF ring cores in annonaceous acetogenins

Organic Letters

Volumn 5, Issue 9, 2003, Pages 1411-1414

  Maezaki, Naoyoshi ^a   Kojima, Naoto ^a   Tominaga, Hiroaki ^a   Yanai, Minori ^a   Tanaka, Tetsuaki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOGENIN; ALDEHYDE; ALKYNYL GROUP; TETRAHYDROFURAN; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG ACTIVITY; DRUG SYNTHESIS; ISOMER; METHODOLOGY; STEREOCHEMISTRY;

EID: 0141519346     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034131r     Document Type: Article

References (35)

1. For recent reviews for annonaceous acetogenins, see: (a) Alali, F. Q.; Liu, X.-X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504-540. (b) Zafra-Polo, M. C.; Figadère, B.; Gallardo, T.; Tormo, J. R.; Cortes, D. Phytochemistry 1998, 48, 1087-1117. (c) Cavé, A.; Figadére, B.; Laurens, A.; Cortes D. In Progress in the Chemistry of Organic Natural Products: Acetogenins from Annonaceae; Hertz, W., Eds.; Springer-Verlag: New York, 1997; Vol. 70, pp 81-288. (d) Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 13, 275-306. (e) Zafra-Polo, M. C.; González, M. C.; Estornell, E.; Sahpaz, S.; Cortes, D. Phytochemistry 1996, 42, 253-271. (f) Gu, Z.-M.; Zhao, G.-X.; Oberlies, N. H.; Zeng, L.; McLaughlin, J. L. In Recent Advances in Phytochemistry: ANNONACEOUS ACETOGENINS; Arnason, J. T., Mata, R., Romeo, J. T., Eds.; Plenum Press: New York, 1995; Vol. 29, pp 249-310. (g) Fang, X.-P.; Rieser, M. J.; Gu, Z.-M.; Zhao, G.-X.; McLaughlin, J. L. Phytochem. Anal. 1993, 4, 27-67. (h) Rupprecht, J. K.; Hui, Y.-H.; McLaughlin, J. L. J. Nat. Prod. 1990, 53, 237-278.
2. For recent reviews for annonaceous acetogenins, see: (a) Alali, F. Q.; Liu, X.-X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504-540. (b) Zafra-Polo, M. C.; Figadère, B.; Gallardo, T.; Tormo, J. R.; Cortes, D. Phytochemistry 1998, 48, 1087-1117. (c) Cavé, A.; Figadére, B.; Laurens, A.; Cortes D. In Progress in the Chemistry of Organic Natural Products: Acetogenins from Annonaceae; Hertz, W., Eds.; Springer-Verlag: New York, 1997; Vol. 70, pp 81-288. (d) Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 13, 275-306. (e) Zafra-Polo, M. C.; González, M. C.; Estornell, E.; Sahpaz, S.; Cortes, D. Phytochemistry 1996, 42, 253-271. (f) Gu, Z.-M.; Zhao, G.-X.; Oberlies, N. H.; Zeng, L.; McLaughlin, J. L. In Recent Advances in Phytochemistry: ANNONACEOUS ACETOGENINS; Arnason, J. T., Mata, R., Romeo, J. T., Eds.; Plenum Press: New York, 1995; Vol. 29, pp 249-310. (g) Fang, X.-P.; Rieser, M. J.; Gu, Z.-M.; Zhao, G.-X.; McLaughlin, J. L. Phytochem. Anal. 1993, 4, 27-67. (h) Rupprecht, J. K.; Hui, Y.-H.; McLaughlin, J. L. J. Nat. Prod. 1990, 53, 237-278.
3. For recent reviews for annonaceous acetogenins, see: (a) Alali, F. Q.; Liu, X.-X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504-540. (b) Zafra-Polo, M. C.; Figadère, B.; Gallardo, T.; Tormo, J. R.; Cortes, D. Phytochemistry 1998, 48, 1087-1117. (c) Cavé, A.; Figadére, B.; Laurens, A.; Cortes D. In Progress in the Chemistry of Organic Natural Products: Acetogenins from Annonaceae; Hertz, W., Eds.; Springer-Verlag: New York, 1997; Vol. 70, pp 81-288. (d) Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 13, 275-306. (e) Zafra-Polo, M. C.; González, M. C.; Estornell, E.; Sahpaz, S.; Cortes, D. Phytochemistry 1996, 42, 253-271. (f) Gu, Z.-M.; Zhao, G.-X.; Oberlies, N. H.; Zeng, L.; McLaughlin, J. L. In Recent Advances in Phytochemistry: ANNONACEOUS ACETOGENINS; Arnason, J. T., Mata, R., Romeo, J. T., Eds.; Plenum Press: New York, 1995; Vol. 29, pp 249-310. (g) Fang, X.-P.; Rieser, M. J.; Gu, Z.-M.; Zhao, G.-X.; McLaughlin, J. L. Phytochem. Anal. 1993, 4, 27-67. (h) Rupprecht, J. K.; Hui, Y.-H.; McLaughlin, J. L. J. Nat. Prod. 1990, 53, 237-278.
4. For recent reviews for annonaceous acetogenins, see: (a) Alali, F. Q.; Liu, X.-X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504-540. (b) Zafra-Polo, M. C.; Figadère, B.; Gallardo, T.; Tormo, J. R.; Cortes, D. Phytochemistry 1998, 48, 1087-1117. (c) Cavé, A.; Figadére, B.; Laurens, A.; Cortes D. In Progress in the Chemistry of Organic Natural Products: Acetogenins from Annonaceae; Hertz, W., Eds.; Springer-Verlag: New York, 1997; Vol. 70, pp 81-288. (d) Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 13, 275-306. (e) Zafra-Polo, M. C.; González, M. C.; Estornell, E.; Sahpaz, S.; Cortes, D. Phytochemistry 1996, 42, 253-271. (f) Gu, Z.-M.; Zhao, G.-X.; Oberlies, N. H.; Zeng, L.; McLaughlin, J. L. In Recent Advances in Phytochemistry: ANNONACEOUS ACETOGENINS; Arnason, J. T., Mata, R., Romeo, J. T., Eds.; Plenum Press: New York, 1995; Vol. 29, pp 249-310. (g) Fang, X.-P.; Rieser, M. J.; Gu, Z.-M.; Zhao, G.-X.; McLaughlin, J. L. Phytochem. Anal. 1993, 4, 27-67. (h) Rupprecht, J. K.; Hui, Y.-H.; McLaughlin, J. L. J. Nat. Prod. 1990, 53, 237-278.
5. For recent reviews for annonaceous acetogenins, see: (a) Alali, F. Q.; Liu, X.-X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504-540. (b) Zafra-Polo, M. C.; Figadère, B.; Gallardo, T.; Tormo, J. R.; Cortes, D. Phytochemistry 1998, 48, 1087-1117. (c) Cavé, A.; Figadére, B.; Laurens, A.; Cortes D. In Progress in the Chemistry of Organic Natural Products: Acetogenins from Annonaceae; Hertz, W., Eds.; Springer-Verlag: New York, 1997; Vol. 70, pp 81-288. (d) Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 13, 275-306. (e) Zafra-Polo, M. C.; González, M. C.; Estornell, E.; Sahpaz, S.; Cortes, D. Phytochemistry 1996, 42, 253-271. (f) Gu, Z.-M.; Zhao, G.-X.; Oberlies, N. H.; Zeng, L.; McLaughlin, J. L. In Recent Advances in Phytochemistry: ANNONACEOUS ACETOGENINS; Arnason, J. T., Mata, R., Romeo, J. T., Eds.; Plenum Press: New York, 1995; Vol. 29, pp 249-310. (g) Fang, X.-P.; Rieser, M. J.; Gu, Z.-M.; Zhao, G.-X.; McLaughlin, J. L. Phytochem. Anal. 1993, 4, 27-67. (h) Rupprecht, J. K.; Hui, Y.-H.; McLaughlin, J. L. J. Nat. Prod. 1990, 53, 237-278.
6. For recent reviews for annonaceous acetogenins, see: (a) Alali, F. Q.; Liu, X.-X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504-540. (b) Zafra-Polo, M. C.; Figadère, B.; Gallardo, T.; Tormo, J. R.; Cortes, D. Phytochemistry 1998, 48, 1087-1117. (c) Cavé, A.; Figadére, B.; Laurens, A.; Cortes D. In Progress in the Chemistry of Organic Natural Products: Acetogenins from Annonaceae; Hertz, W., Eds.; Springer-Verlag: New York, 1997; Vol. 70, pp 81-288. (d) Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 13, 275-306. (e) Zafra-Polo, M. C.; González, M. C.; Estornell, E.; Sahpaz, S.; Cortes, D. Phytochemistry 1996, 42, 253-271. (f) Gu, Z.-M.; Zhao, G.-X.; Oberlies, N. H.; Zeng, L.; McLaughlin, J. L. In Recent Advances in Phytochemistry: ANNONACEOUS ACETOGENINS; Arnason, J. T., Mata, R., Romeo, J. T., Eds.; Plenum Press: New York, 1995; Vol. 29, pp 249-310. (g) Fang, X.-P.; Rieser, M. J.; Gu, Z.-M.; Zhao, G.-X.; McLaughlin, J. L. Phytochem. Anal. 1993, 4, 27-67. (h) Rupprecht, J. K.; Hui, Y.-H.; McLaughlin, J. L. J. Nat. Prod. 1990, 53, 237-278.
7. For recent reviews for annonaceous acetogenins, see: (a) Alali, F. Q.; Liu, X.-X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504-540. (b) Zafra-Polo, M. C.; Figadère, B.; Gallardo, T.; Tormo, J. R.; Cortes, D. Phytochemistry 1998, 48, 1087-1117. (c) Cavé, A.; Figadére, B.; Laurens, A.; Cortes D. In Progress in the Chemistry of Organic Natural Products: Acetogenins from Annonaceae; Hertz, W., Eds.; Springer-Verlag: New York, 1997; Vol. 70, pp 81-288. (d) Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 13, 275-306. (e) Zafra-Polo, M. C.; González, M. C.; Estornell, E.; Sahpaz, S.; Cortes, D. Phytochemistry 1996, 42, 253-271. (f) Gu, Z.-M.; Zhao, G.-X.; Oberlies, N. H.; Zeng, L.; McLaughlin, J. L. In Recent Advances in Phytochemistry: ANNONACEOUS ACETOGENINS; Arnason, J. T., Mata, R., Romeo, J. T., Eds.; Plenum Press: New York, 1995; Vol. 29, pp 249-310. (g) Fang, X.-P.; Rieser, M. J.; Gu, Z.-M.; Zhao, G.-X.; McLaughlin, J. L. Phytochem. Anal. 1993, 4, 27-67. (h) Rupprecht, J. K.; Hui, Y.-H.; McLaughlin, J. L. J. Nat. Prod. 1990, 53, 237-278.
8. For recent reviews for annonaceous acetogenins, see: (a) Alali, F. Q.; Liu, X.-X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504-540. (b) Zafra-Polo, M. C.; Figadère, B.; Gallardo, T.; Tormo, J. R.; Cortes, D. Phytochemistry 1998, 48, 1087-1117. (c) Cavé, A.; Figadére, B.; Laurens, A.; Cortes D. In Progress in the Chemistry of Organic Natural Products: Acetogenins from Annonaceae; Hertz, W., Eds.; Springer-Verlag: New York, 1997; Vol. 70, pp 81-288. (d) Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 13, 275-306. (e) Zafra-Polo, M. C.; González, M. C.; Estornell, E.; Sahpaz, S.; Cortes, D. Phytochemistry 1996, 42, 253-271. (f) Gu, Z.-M.; Zhao, G.-X.; Oberlies, N. H.; Zeng, L.; McLaughlin, J. L. In Recent Advances in Phytochemistry: ANNONACEOUS ACETOGENINS; Arnason, J. T., Mata, R., Romeo, J. T., Eds.; Plenum Press: New York, 1995; Vol. 29, pp 249-310. (g) Fang, X.-P.; Rieser, M. J.; Gu, Z.-M.; Zhao, G.-X.; McLaughlin, J. L. Phytochem. Anal. 1993, 4, 27-67. (h) Rupprecht, J. K.; Hui, Y.-H.; McLaughlin, J. L. J. Nat. Prod. 1990, 53, 237-278.
9. Recent reviews for a synthesis of acetogenins, see: (a) Elliott, M. C.; Williams, E. J. Chem. Soc., Perkin Trans. 1 2001, 2303-2340. (b) Elliott, M. C. J. Chem. Soc., Perkin Trans. 1 2000, 1291-1318. (c) Casiraghi, G.; Zanardi, F.; Battistini, L.; Rassu, G. Chemtracts - Org. Chem. 1998, 11, 803-827. (d) Elliott, M. C. J. Chem. Soc., Perkin Trans. 1 1998, 4175-4200. (e) Figadère, B. Acc. Chem. Res. 1995, 28, 359-365. (f) Hoppe, R.; Scharf, H.-D. Synthesis 1995, 1447-1464. (g) Koert, U. Synthesis 1995, 115-132.
10. Recent reviews for a synthesis of acetogenins, see: (a) Elliott, M. C.; Williams, E. J. Chem. Soc., Perkin Trans. 1 2001, 2303-2340. (b) Elliott, M. C. J. Chem. Soc., Perkin Trans. 1 2000, 1291-1318. (c) Casiraghi, G.; Zanardi, F.; Battistini, L.; Rassu, G. Chemtracts - Org. Chem. 1998, 11, 803-827. (d) Elliott, M. C. J. Chem. Soc., Perkin Trans. 1 1998, 4175-4200. (e) Figadère, B. Acc. Chem. Res. 1995, 28, 359-365. (f) Hoppe, R.; Scharf, H.-D. Synthesis 1995, 1447-1464. (g) Koert, U. Synthesis 1995, 115-132.
11. Recent reviews for a synthesis of acetogenins, see: (a) Elliott, M. C.; Williams, E. J. Chem. Soc., Perkin Trans. 1 2001, 2303-2340. (b) Elliott, M. C. J. Chem. Soc., Perkin Trans. 1 2000, 1291-1318. (c) Casiraghi, G.; Zanardi, F.; Battistini, L.; Rassu, G. Chemtracts - Org. Chem. 1998, 11, 803-827. (d) Elliott, M. C. J. Chem. Soc., Perkin Trans. 1 1998, 4175-4200. (e) Figadère, B. Acc. Chem. Res. 1995, 28, 359-365. (f) Hoppe, R.; Scharf, H.-D. Synthesis 1995, 1447-1464. (g) Koert, U. Synthesis 1995, 115-132.
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