A highly efficient synthesis of (S)-(+)-N-Boc-coniine using ring- closing olefin metathesis (RCM)

Tetrahedron Letters

Volumn 40, Issue 30, 1999, Pages 5581-5582

  Jo, Eunyoung ^a   Na, Youngim ^a   Chang, Sukbok ^a  

^a Ewha Womans University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AMINO ACID; CONIINE; NORVALINE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROGENATION; SYNTHESIS;

EID: 0033165925     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01081-3     Document Type: Article

References (16)

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2. (b) Schneider, M. J. In Alkaloids: Chemical & Biological Perspectives; Pelletier, S. M., Ed.; Pergamon: Oxford, 1996; Vol 10, Chapter 2, p. 155.
3. (a) Enders, D.; Tiebes, J. Liebigs Ann. Chem. 1993, 173.
4. (b) Reding, M. T.; Buchwald, S. L. J. Org. Chem. 1998, 63, 6344.
5. (c) Davies, S. B.; McKervey, M. A. Tetrahedron Lett. 1999, 40, 1229, and references cited therein.
6. 13C NMR, IR and HRMS.
7. Williams, D. R.; Kissel, W. S. J. Am. Chem. Soc. 1998, 120, 11198.
8. Kotsuki, H.; Kadota, I.; Ochi, M. J. Org. Chem. 1990, 55, 4417.
9. For recent reviews on olefin metathesis see: (a) Ivin, K. J. J. Mol. Cat. A-Chem. 1998, 133, 1.
10. (b) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
11. (c) Randall, M. L.; Snapper, M. L. J. Mol. Cat. A-Chem. 1998, 133, 29.
12. It was previously shown that piperidine ring systems could be either in general or for specific purposes constructed using ring-closing metathesis: (a) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324.
13. (b) Huwe, C. M.; Kiehl, O. C.; Blechert, S. Synlett 1996, 65.
14. (c) Rutjes, F. P. J. T.; Schoemaker, H. E. Tetrahedron Lett. 1997, 38, 677.
15. + 224.1650, found 224.1648.
16. 3).