A catalytic asymmetric synthesis of tubifolidine

Journal of Organic Chemistry

Volumn 63, Issue 21, 1998, Pages 7547-7551

  Shimizu, Satoshi ^a   Ohori, Ken ^a   Arai, Takayoshi ^a   Sasai, Hiroaki ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000221935     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981069g     Document Type: Article

References (25)

1. The Institute of Scientific and Industrial Research, Osaka University, 8-1 Mihogaoka, Ibaraki, Osaka 567-0047, Japan
2. For a review, see: Bosch, J.; Bonjoch, J.; Amot, M. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1996; vol. 48, pp 75-189.
3. (a) (±)-2: Amat, M.; Linares, A.; Bosch, J. J. Org. Chem. 1990, 55, 6299-6312 and references therein.
4. (b) (±)-1: Bonjoch, J.; Sóle, D.; Garcia-Rubio, S.; Bosch, J. J. Am. Chem. Soc. 1997, 119, 7230-7240 and references therein. See also ref 3a.
5. (-)-1: Amat, M.; Coll, M.-D.; Bosch, J.; Espinosa, E.; Molins, E. Tetrahedron Asymmetry 1997, 8, 935-948. See also ref 3b.
6. (±)-strychnine: Kuehne, M. E.; Xu, F. J. Org. Chem. 1993, 58, 7490-7497.
7. Rawal, V. H.; Iwasa, S. J. Org. Chem. 1994, 59, 2685-2686 and references therein.
8. (e) (-)-strychnine: Magnus, P.; Giles, M.; Bonnert, R.; Johnson, G.; McQuire, L.; Deluca, M.; Merritt, A.; Kim, C. S.; Vicker, N. J. Am. Chem. Soc. 1993, 115, 8116-8129.
9. Knight, S. D.; Overman, L. E.; Pairaudeau, G. J. Am. Chem. Soc. 1995, 117, 5776-5788 and references therein.
10. Magnus, P.; Sear, N. L.; Kim, C. S.; Vicker, N. J. Org. Chem. 1992, 57, 70-78. In this paper, the resolution of cyclohexanone-3-acetic acid using quinine was also described.
11. For a review, see: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1236-1256.
12. (a) Arai, T.; Yamada, Y. M. A.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem. Eur. J. 1996, 2, 1368-1378.
13. (b) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441-442.
14. Molecular sieves (MS) 4A was dried at 180°C for 6 h under reduced pressure prior to use.
15. The absolute configuration of 5 has already been determined. See: Sasai, H.; Arai, T.; Satow, Y.; Houk. K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198. The enantiomeric excess was determined by chiral stationary phase HPLC analysis [DAICEL CHIRALPAK AS, hexane/2-propanol (90:10, v/v), flow rate: 0.5 mL/min, retention time: 50 min (R)-isomer and 60 min (S)-isomer, detection at 215 nm].
16. Berger, L.; Corraz, A. J. U.S. Patent 4,009,181, 1977.
17. The enantiomeric excess was determined by chiral stationary phase HPLC analysis [DAICEL CHIRALPAK AD, hexane/2-propanol (90:10, v/v), flow rate: 1.0 mL/min, retention time: 14 min (S)-isomer and 17 min (R)-isomer, detection at 254 nm].
18. 2O gives tetrahydrocarbazol-4-one. See also ref 4.
19. Trost, B. M.; Murayama, E. J. Am. Chem. Soc. 1981, 103, 6529-6530.
20. (a) Mattson, R. J.; Pham, K. M.; Leuck, D. J.; Cowen, K. A. J. Org. Chem. 1990, 55, 2552-2554.
21. (b) Bhattacharyya, S. Tetrahedron Lett. 1994, 35, 2401-2404.
22. We also tried to apply this type of reaction with DDQ to the other substrates. The desired tetracyclic compound i, however, could not be obtained at all, most likely due to the steric hindrance of the ethyl group. On the other hand, ii could be obtained in moderate yield.
23. The C-4 epimer was also obtained in 9% overall yield. The stereochemistry of the epimers could be confirmed by carrying out NOE measurements.
24. The enantiomeric excess was confirmed by chiral stationary phase HPLC analysis, ref 3c.
25. For the isolation and structural elucidation of this alkaloid, see: Kump, W. G.; Patel, M. B.; Rowson, J. M.; Schmid, H. Helv. Chim. Acta 1964, 47, 1497-1503.