Ytterbium(III) trifluoromethanesulfonate catalyzed high pressure reaction of epoxides with indole. An enantioselective synthesis of (+)-diolmycin A21

Tetrahedron Letters

Volumn 37, Issue 21, 1996, Pages 3727-3730

  Kotsuki, Hiyoshizo ^a   Teraguchi, Masahiro ^a   Shimomoto, Nami ^a   Ochi, Masamitsu ^a  

^a KOCHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DIOLMYCIN A2; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029993244     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00670-3     Document Type: Article

References (25)

1. High Pressure Organic Chemistry. Part 20. For Part 19, see: Kotsuki, H.; Hayashida, K.; Shimanouchi, T.; Nishizawa, H. J. Org. Chem. 1996, 61, 984-990.
2. Kotsuki, H.; Nishiuchi, M.; Kobayashi, S.; Nishizawa, H. J. Org. Chem. 1990, 55, 2969-2972; Kotsuki, H.; Hayakawa, H.; Wakao, M.; Shimanouchi, T.; Ochi, M. Tetrahedron: Asymmetry 1995, 6, 2665-2668.
3. Kotsuki, H.; Nishiuchi, M.; Kobayashi, S.; Nishizawa, H. J. Org. Chem. 1990, 55, 2969-2972; Kotsuki, H.; Hayakawa, H.; Wakao, M.; Shimanouchi, T.; Ochi, M. Tetrahedron: Asymmetry 1995, 6, 2665-2668.
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5. Kobayashi, S. Synlett 1994, 689-701; Kobayashi, S. Yuki Gosei Kagaku Kyokai-shi 1995, 53, 370-380.
6. For some related works, see: (a) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597-2601.
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9. (d) Meguro, M.; Asao, N.; Yamamoto, Y. ibid. 1994, 35, 7395-7398.
10. For some other applications of lanthanide catalysts to high pressure transformations, see: Posner, G. H.; Ishihara, Y. Tetrahedron Lett. 1994, 35, 7545-7548; Jenner, G. ibid. 1995, 36, 233-236; Carretero, J. C.; Ruano, J. L. G.; Cabrejas, L. M. M. Tetrahedron 1995, 51, 8323-8332; Vandenput, D. A. L.; Scheeren, H. W. ibid. 1995, 57, 8383-8388.
11. For some other applications of lanthanide catalysts to high pressure transformations, see: Posner, G. H.; Ishihara, Y. Tetrahedron Lett. 1994, 35, 7545-7548; Jenner, G. ibid. 1995, 36, 233-236; Carretero, J. C.; Ruano, J. L. G.; Cabrejas, L. M. M. Tetrahedron 1995, 51, 8323-8332; Vandenput, D. A. L.; Scheeren, H. W. ibid. 1995, 57, 8383-8388.
12. For some other applications of lanthanide catalysts to high pressure transformations, see: Posner, G. H.; Ishihara, Y. Tetrahedron Lett. 1994, 35, 7545-7548; Jenner, G. ibid. 1995, 36, 233-236; Carretero, J. C.; Ruano, J. L. G.; Cabrejas, L. M. M. Tetrahedron 1995, 51, 8323-8332; Vandenput, D. A. L.; Scheeren, H. W. ibid. 1995, 57, 8383-8388.
13. For some other applications of lanthanide catalysts to high pressure transformations, see: Posner, G. H.; Ishihara, Y. Tetrahedron Lett. 1994, 35, 7545-7548; Jenner, G. ibid. 1995, 36, 233-236; Carretero, J. C.; Ruano, J. L. G.; Cabrejas, L. M. M. Tetrahedron 1995, 51, 8323-8332; Vandenput, D. A. L.; Scheeren, H. W. ibid. 1995, 57, 8383-8388.
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18. Freshly dried solvents were used for all reactions. The unreacted indole was cleanly recovered, while the starting epoxide was completely decomposed under these conditions.
19. Review: Kotsuki, H. Kagaku to Kogyo (Osaka) 1994, 68, 265-278.
20. Satisfactory spectral and analytical data were obtained for all new compounds.
21. Kotsuki, H.; Kuzume, H.; Gohda, T.; Fukuhara, M.; Ochi, M.; Oishi, T.; Hirama, M.; Shiro, M. Tetrahedron: Asymmetry 1995, 6, 2227-2236, and references cited therein.
22. Kotsuki, H.; Kadota, I.; Ochi, M. J. Org. Chem. 1990, 55, 4417-4422.
23. 6d
24. 3: 297.1365; found: 297.1362.
25. 13C NMR) of an authentic sample and information on the optical purity of the natural substance.