Total synthesis of (+)-4-deoxygigantecin

Tetrahedron Letters

Volumn 38, Issue 24, 1997, Pages 4247-4250

  Makabe, Hidefumi ^a   Tanaka, Akira ^a   Oritani, Takayuki ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOGENIN;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0031006992     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00856-3     Document Type: Article

References (24)

1. a) Rupprecht, J. K.; Hui, Y. -H.; McLaughlin, J. L.; J. Nat. Prod., 1990, 53, 237.
2. b) Fang, X. -P.; Rieser, M. J.; Gu, Z. -M.; Zhao, G. -X.; McLaghlin, J. L.; Phytochem. Anal., 1993, 4, 27, 49.
3. c) Cavé, A.; Cortes, D.; Figadère, B.; Hoquemoller, R.; Laprévote, O.; Laurens, A.; Leboeuf, M. Phytochemical Potential of Tropical Plants. In Recent Advances in Phytochemistry; Downum, K. R.; Romeo, J. T.; Stafford, H. A. Eds.; Plenum Press: New York, 1993; pp. 167-202.
4. d) Gu, Z. -M.; Zhao, G. -X.; Oberlies, N. H.; Zeng, L.; McLaughlin, J. L. Annonaceous Acetogenins: Potent Mitochondrial Inhibitors with Diverse Applications. In Recent Advances in Phytochemistry; Arnason, J. T.; Mata, R.; Romeo, J. T. Eds.; Plenum Press: New York, 1995; pp. 249-310.
5. e) ZafraPolo, M. C.; Gonzalez, M. C.; Estornell, E.; Sahpaz, S.; Cortes, D.; Phytochemistry, 1996, 42, 253.
6. 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.
7. a) Figadère, B.; Acc. Chem. Res., 1995, 28, 359 and references cited therein,
8. b) Hoye, T. R.; Ye, Z.; J. Am. Chem. Sos., 1996, 118, 1801 and references cited therein.
9. c) Konno, H.; Makabe, H.; Tanaka, A.; Oritani, T.; Tetrahedron Lett., 1996, 37, 5393.
10. d) Makabe, H.; Tanimoto, H.; Tanaka, A.; Oritani, T.; Heterocycles, 1996, 43, 2229.
11. Fang, X. -P.; Anderson, J. E.; Smith, D. L.; Wood, K. V.; McLaughlin, J. L.; Heterocycles, 1992, 34, 1075.
12. Makabe, H.; Tanaka, A.; Oritani, T.; Biosci. Biotech. Biochem., 1993, 57, 1028.
13. Makabe, H.; Tanaka, A.; Oritani, T.; J. Chem. Soc. Perkin Trans. I, 1994, 1975.
14. Hoye, T. R.; Hanson, P. R.; Tetrahedron Lett., 1993, 34, 5043.
15. a) Yamaguchi, M.; Hirao, I.; Tetrahedron Lett., 1983, 24, 391.
16. b) Yamaguchi, M.; Nobayashi, Y.; Hirao, I.; Tetrahedron Lett., 1983, 24, 5121.
17. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B.; Chem. Rev., 1994, 94, 2483.
18. 7Na; 577.4080 Found; 577.4091.
19. White, J. D.; Somers, T. C.; Reddy, G. N.; J. Org. Chem., 1992, 57, 4991.
20. Cox, G. G.; Moody, C. J.; Austin, D. J.; Padwa, A.; Tetrahedron., 1993, 49, 5109.
21. Takai, K.; Nitta, K.; Utimoto, K.; J. Am. Chem. Soc., 1986, 108, 7408.
22. Hoye, T. R.; Hanson, P. R.; Kovelesky, A. C; Ocain, T. D.; Zhuang, Z.; J. Am. Chem. Soc., 1991, 113, 9369.
23. Naito, H.; Kawahara, K.; Maruta, K.; Maeda, M.; Sasaki, S.; J. Org. Chem., 1995, 60, 4419.
24. 3, 500 MHz) δ : 0.88 (3H, t, J=6.8 Hz), 1.40 (3H, d, J=6.9 Hz), 1.21∼1.80 (42H, m), 1.99 (4H, m), 2.15 (1H, br. OH), 2.26 (2H, tt, J= 7.3, 1.5 Hz), 2.40 (1H, br. OH), 2.65 (1H, br. OH), 3.40∼3.45 (3H, m), 3.80∼3.89 (4H, m), 5.00 (1H, dq, J=6.8, 1.5 Hz), 6.99 (1H, d, J=1.5 Hz).