An expeditious total synthesis of the natural stereomeric mixture of stenusine following a possible biogenetic pathway

Angewandte Chemie - International Edition

Volumn 39, Issue 8, 2000, Pages 1493-1495

  Poupon, Erwan ^a   Kunesch, Nicole ^a   Husson, Henri Philippe ^a  

^a FACULTÉ DES SCIENCES PHARMACEUTIQUES ET BIOLOGIQUES   (France)

Author keywords

Alkaloids; Asymmetric synthesis; Biomimetic synthesis; Enamines

Indexed keywords

PIPERIDINE DERIVATIVE; STENUSINE; UNCLASSIFIED DRUG;

ARTICLE; RACEMIC MIXTURE; REACTION ANALYSIS; SYNTHESIS;

EID: 0034678589     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (20)

1. a) H. Schildknecht, D. Krauss, J. Connert, H. Essenbreis, N. Orfanides, Angew. Chem. 1975, 87, 421; Angew. Chem. Int. Ed. Engl. 1975, 14, 427;
2. a) H. Schildknecht, D. Krauss, J. Connert, H. Essenbreis, N. Orfanides, Angew. Chem. 1975, 87, 421; Angew. Chem. Int. Ed. Engl. 1975, 14, 427;
3. b) H. Schildknecht, D. Berger, D. Krauss, J. Connert, J. Gehlhaus, H. Essenbreis, J. Chem. Ecol. 1976, 2, 1-11.
4. a) C. Stevens, N. De Kimpe, J. Org. Chem. 1993, 58, 132-134;
5. b) S. Heilporn, J.-C. Brackman, D. Daloze, Nat. Prod. Lett. 1997, 10, 193-200.
6. a) D. Enders, J. Tiebes, N. De Kimpe, M. Keppens, C. Stevens, G. Smagghe, O. Betz, J. Org. Chem. 1993, 58, 4881-4884;
7. b) L. Micouin, T. Varesa, C. Riche, A. Chiaroni, J.-C. Quirion, H.-P. Husson, Tetrahedron Lett. 1994, 35, 2529-2532.
8. a) D. François, M.-C. Lallemand, M. Selkti, A. Tomas, N. Kunesch, H.-P. Husson, J. Org. Chem. 1997, 62, 8914-8916;
9. b) D. François, M.-C. Lallemand, M. Selkti, A. Tomas, N. Kunesch, H.-P. Husson, Angew. Chem. 1998, 110, 112-114; Angew. Chem. Int. Ed. 1998, 37, 104-105.
10. b) D. François, M.-C. Lallemand, M. Selkti, A. Tomas, N. Kunesch, H.-P. Husson, Angew. Chem. 1998, 110, 112-114; Angew. Chem. Int. Ed. 1998, 37, 104-105.
11. Observed as a noncharacterized by-product: Y.-S. Wong, C. Marazano, D. Gnecco, B. C. Das, Tetrahedron Lett. 1994, 35, 707-710.
12. D. J. White, G. L. Bolton, A. P. Dantanarayana, C. M. J. Fox, R. N. Hiner, R. W. Jackson, K. Sakuma, U. S. Warrier, J. Am. Chem. Soc. 1995, 117, 1908-1939.
13. A. A. Frimer, Chem. Rev. 1979, 79, 359-387.
14. a) E. Wenkert, K. G. Dave, F. Haglid, R. G. Lewis, T. Oishi, R. V. Stevens, M. Terashima, J. Org. Chem. 1968, 33, 747-753;
15. b) K. Tsubata, Y. Sugihara, Tetrahedron Lett. 1982, 23, 1201-1204.
16. This unusual reaction was also observed with acetaldehyde and phenylacetaldehyde in the presence of air, providing aldehyde 6 in 16% and 10% yield, respectively.
17. W. Meise, Methoden Org. Chem. (Houben-Weyl), 4th ed. 1980-, Vol. 4/1c, p. 257.
18. S. C. Benson, P. Cai, M. Colon, M. A. Haiza, M. Tokles, J. K. Snyder, J. Org. Chem. 1988, 53, 5335-5341.
19. The carbon resonances were assigned by 2D experiments.
20. H. Breitmaier, Structure Elucidation by NMR in Organic Chemistry, Wiley, New York, 1995.