Development of a flexible approach to Nuphar alkaloids via two enantiospecific piperidine-forming reactions

Journal of Organic Chemistry

Volumn 70, Issue 1, 2005, Pages 207-213

  Goodenough, Katharine M ^a   Moran, Wesley J ^a   Raubo, Piotr ^b   Harrity, Joseph P A ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b NEUROSCIENCE RESEARCH CENTRE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; AMINES; CHEMICAL REACTIONS; SYNTHESIS (CHEMICAL);

EXOCYCLIC ALKENES; LACTAM; NUPHAR ALKALOIDS; STEREOSELECTIVE SYNTHESIS;

OLEFINS;

ALKALOID; ALKENE; AZIRIDINE; CASTORAMINE; DEOXYNUPHARIDINE; FUNCTIONAL GROUP; LACTAM; NUPHAROLUTINE; PALLADIUM; PIPERIDINE; PIPERIDINE DERIVATIVE; PLANT EXTRACT; QUINOLIZIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; MITSUNOBU REACTION; NUPHAR; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

ALKALOIDS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; LACTAMS; MOLECULAR STRUCTURE; NUPHAR; PALLADIUM; PIPERIDINES; PLANTS, MEDICINAL; QUINOLIZINES; STEREOISOMERISM;

EID: 11844292757     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048455k     Document Type: Article

References (33)

1. (a) Strunzand, G. M.; Finlay, J. A. In The Alkaloids; Brossi, A., Ed.; Academic Press: San Diego, 1986; Vol. 26, p 89.
2. (b) Buffat, M. G. P. Tetrahedron 2004, 60, 1701.
3. (a) LaLonde, R. T.; Wong, C.-F.; Das, K. C. J. Am. Chem. Soc. 1972, 94, 8522.
4. (b) Maurer, B.; Ohloof, G. Helv. Chim. Acta 1976, 59, 1169.
5. Miyazawa, M.; Yoshio, K.; Ishikawa, Y.; Kameoka, H. J. Agric. Food Chem. 1998, 46, 1059.
6. (a) Matsuda, H.; Shimoda, H.; Yoshikawa, M. Bioorg. Med. Chem. 2001, 9, 1031.
7. (b) Matsuda, H.; Morikawa, T.; Oda, M.; Asao, Y.; Yoshikawa, M. Bioorg. Med. Chem. Lett. 2003, 13, 4445.
8. Bohlmann, F.; Winterfeldt, E.; Laurent, H.; Ude, W. Tetrahedron 1963, 19, 195.
9. For recent approaches see: (a) Hwang, Y. C.; Fowler, F. J. Org. Chem. 1985, 50, 2719. (b) Hwang, Y. C.; Chu, M.; Fowler, F. J. Org. Chem. 1985, 50, 0, 3885. (c) Yasuda, S.; Hanaoka, M.; Arata, Y. Chem. Pharm. Bull. 1980, 28, 831. (d) Szychowski, J.; Leniewski, A.; Wrobel, J. T. Chem. Ind. (London) 1978, 273.
10. For recent approaches see: (a) Hwang, Y. C.; Fowler, F. J. Org. Chem. 1985, 50, 2719. (b) Hwang, Y. C.; Chu, M.; Fowler, F. J. Org. Chem. 1985, 50, 0, 3885. (c) Yasuda, S.; Hanaoka, M.; Arata, Y. Chem. Pharm. Bull. 1980, 28, 831. (d) Szychowski, J.; Leniewski, A.; Wrobel, J. T. Chem. Ind. (London) 1978, 273.
11. For recent approaches see: (a) Hwang, Y. C.; Fowler, F. J. Org. Chem. 1985, 50, 2719. (b) Hwang, Y. C.; Chu, M.; Fowler, F. J. Org. Chem. 1985, 50, 0, 3885. (c) Yasuda, S.; Hanaoka, M.; Arata, Y. Chem. Pharm. Bull. 1980, 28, 831. (d) Szychowski, J.; Leniewski, A.; Wrobel, J. T. Chem. Ind. (London) 1978, 273.
12. For recent approaches see: (a) Hwang, Y. C.; Fowler, F. J. Org. Chem. 1985, 50, 2719. (b) Hwang, Y. C.; Chu, M.; Fowler, F. J. Org. Chem. 1985, 50, 0, 3885. (c) Yasuda, S.; Hanaoka, M.; Arata, Y. Chem. Pharm. Bull. 1980, 28, 831. (d) Szychowski, J.; Leniewski, A.; Wrobel, J. T. Chem. Ind. (London) 1978, 273.
13. Barluenga, J.; Aznar, F.; Ribas, C.; Valdés, C. J. Org. Chem. 1999, 64, 3736.
14. (a) Medley, S. J.; Moran, W. J.; Prenzel, A. H. G. P.; Price, D. A.; Harrity, J. P. A. Synlett 2001, 1596.
15. (b) Hedley, S. J.; Moran, W. J.; Price, D. A.; Harrity, J. P. A. J. Org. Chem. 2003, 68, 4286.
16. For a preliminary report on our studies toward Nuphar alkaloids see: Moran, W. J.; Goodenough, K. M.; Raubo, P.; Harrity, J. P. A. Org. Lett. 2003, 5, 3427.
17. For a comprehensive review see: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1.
18. Park, J.-I.; Tian, G. R.; Kim, D. H. J. Org. Chem. 2001, 66, 3696.
19. The relative stereochemistry of 12 was assigned by X-ray crystallography. Crystallographic data for 12 have been deposited with the CCDC as Supplementary Publication Number CCDC 210220.
20. Humphrey, J. M.; Bridges, R. J.; Hart, J. A.; Chamberlin, A. R. J. Org. Chem. 1994, 59, 2467.
21. Hanessian, S.; Vanasse, B. Can. J. Chem. 1993, 71, 1401.
22. Wang, J.; Hou, Y.; Wu, P.; Qu, Z.; Chan, A. S. C. Tetrahedron: Asymmetry 1999, 10, 4553.
23. Tsunoda, T.; Ozaki, F.; Ito, S. Tetrahedron Lett. 1993, 34, 1639.
24. Related alkylation products have been observed in [3 + 2] cycloaddition reactions: (a) Trost, B. M.; Chan, D. M. T. J. Am. Chem. Soc. 1983, 105, 2315. (b) Naz, N.; Al-Tel, T. H.; Al-Abed, Y.; Voelter W.; Ficker, R.; Hiller, W. J. Org. Chem. 1996, 61, 3250
25. Related alkylation products have been observed in [3 + 2] cycloaddition reactions: (a) Trost, B. M.; Chan, D. M. T. J. Am. Chem. Soc. 1983, 105, 2315. (b) Naz, N.; Al-Tel, T. H.; Al-Abed, Y.; Voelter W.; Ficker, R.; Hiller, W. J. Org. Chem. 1996, 61, 3250
26. We investigated various analogues of 17 bearing TBDPS, TES ethers, and acetate, but these showed similar reactivities.
27. The double deprotonation of 21 is the first step in the preparation of conjunctive reagent 15: Trost, B. M.; Chan, D. M. T.; Nanninga, T. N. Org. Synth. 1984, 62, 58.
28. Hudlicky, T.; Sinai-Zingde, G.; Natchus, M. G. Tetrahedron Lett. 1987, 28, 5287.
29. Alonso, D. A.; Andersson, P. G. J. Org. Chem. 1998, 65, 9455.
30. 3 and further COSY and NOESY experiments were carried out that confirmed the stereochemistry of 3 as that depicted in Chart 1. These data are described in full in the Supporting Information.
31. 3 and further COSY and NOESY experiments were carried out that confirmed the stereochemistry of 3 as that depicted in Chart 1. These data are described in full in the Supporting Information.
32. Hydroboration of N-allylpiperidine provides a 9:1 mixture of primary/secondary alcohols: Baboulène, M.; Torregrosa, J.-L.; Spèziale, V.; Lattes, A. Bull. Soc. Chim. Fr. 1980, 565.
33. Gmeiner, P.; Feldman, P. L.; Chu-Moyer, M. Y.; Rapaport, H. J. Org. Chem. 1990, 55, 3068.