Total Synthesis of a New Cytotoxic Acetogenin, Jimenezin, and the Revised Structure

Organic Letters

Volumn 1, Issue 12, 1999, Pages 2025-2028

  Takahashi, Shunya ^a   Maeda, Katsuya ^a   Hirota, Shinsuke ^a   Nakata, Tadashi ^a  

^a RIKEN   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; FURAN DERIVATIVE; ISOMURISOLENIN; JIMENEZIN; LACTONE; PYRAN DERIVATIVE;

ANGIOSPERM; ARTICLE; CHEMISTRY; MEDICINAL PLANT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLANT SEED; SYNTHESIS;

ANGIOSPERMS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; FURANS; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; PLANTS, MEDICINAL; PYRANS; SEEDS;

EID: 0033576417     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991200m     Document Type: Article

References (29)

1. For recent review on Annonaceous acetogenins, see: Zeng, L.; Ye, Q.; Oberlies, H. N.; Shi, G.; Gu, Z. M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 13, 275. Allali, F. Q.; Liu, X.-X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504.
2. For recent review on Annonaceous acetogenins, see: Zeng, L.; Ye, Q.; Oberlies, H. N.; Shi, G.; Gu, Z. M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 13, 275. Allali, F. Q.; Liu, X.-X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504.
3. Chavez, D.; Acevedo, L. A.; Mata, R. J. Nat. Prod. 1998, 61, 419.
4. For other acetogenins as having a THP ring, see the following. (a) Mucocin: Shi, G.; Alfonso, D.; Fatope, M. O.; Zeng, L.; Gu, Z. M.; Zhao, G. X.; He, K.; MacDougal, J. M.; McLaughlin, J. L. J. Am. Chem. Soc. 1995, 117, 10409.
5. (b) Pyranicin and pyragonicin: Alali, F. Q.; Rogers, L.; Zhang, Y.; McLaughlin, J. L. Tetrahedron 1998, 54, 5833.
6. Shi, G.; Kozlowski, J. F.; Schwedler, J. T.; Wood, K. V.; MacDougal, J. M.; McLaughlin, J. L. J. Org. Chem. 1996, 61, 7988.
7. McLaughlin, J. L. In Methods in Plant Biochemistry; Hostettmann, K., Ed.; Academic Press: London, 1991; Vol. 6, p 1. Meyer, B. N.; Ferrigni, N. R.; Putnam, J. E.; Jacobsen, L. B.; Nichola, D. E.; McLaughlin, J. L. Planta Med. 1982, 45, 31
8. McLaughlin, J. L. In Methods in Plant Biochemistry; Hostettmann, K., Ed.; Academic Press: London, 1991; Vol. 6, p 1. Meyer, B. N.; Ferrigni, N. R.; Putnam, J. E.; Jacobsen, L. B.; Nichola, D. E.; McLaughlin, J. L. Planta Med. 1982, 45, 31
9. (a) Takahashi, S.; Nakata, T. Tetrahedron Lett. 1999, 40, 723.
10. (b) Takahashi, S.; Nakata, T. Tetrahedron Lett. 1999, 40, 727.
11. Thompson, D. K.; Hubert, C. N.; Wightman, R. H. Tetrahedron 1993, 49, 3827.
12. All new compounds were fully chracterized by IR, NMR, high-resolution mass spectra, and/or combustion analyses.
13. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4156.
14. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769.
15. The stereochemistry was determined by the modified Mosher's method: (a) Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Org. Chem. 1991, 56, 1296.
16. (b) Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092. See also, Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
17. (b) Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092. See also, Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
18. 2-25 (-0.05, -0.07).
19. Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538.
20. For a review of the use of cyclic sulfates and cyclic sulfites as epoxide-like synthons, see: Lohray, B. B. Synthesis 1992, 1035.
21. Muller, S.; Liepold, B.; Roth, G. J.; Bestmann, H. J. Synlett 1996, 521.
22. (a) Hoye, T. R.; Hanson, P. R.; Kovelsky, A. C.; Ocain, T. D.; Zang, Z. J. Am. Chem. Soc. 1991, 113, 9369.
23. (b) Hoye, T. R.; Hanson. P. R. Tetrahedron Lett. 1993, 34, 5043.
24. (c) Hoye, T. R.; Tan, L. Tetrahedron Lett. 1995, 36, 1981.
25. (d) Hoye, T. R.; Ye, Z. J. Am. Chem. Soc. 1996, 118, 1801.
26. Naito, H.; Kawahara, E.; Maruta, K. Maeda, M.; Sasaki, S. J. Org. Chem. 1995, 60, 4419.
27. + 623.4887, found 623.4890.
28. + 623.4887, found 623.4906.
29. 26 -8.9° (c 0.05, MeOH)}.