A Concise Asymmetric Route to Nuphar Alkaloids. A Formal Synthesis of (-)-Deoxynupharidine

Organic Letters

Volumn 5, Issue 19, 2003, Pages 3427-3429

  Moran, Wesley J ^a   Goodenough, Katharine M ^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

ALKALOID DERIVATIVE; AZIRIDINE; DEOXYNUPHARIDINE; PALLADIUM; PIPERIDINE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL REACTION; CYCLOADDITION; GRIGNARD REACTION; MITSUNOBU REACTION; POLYMERIZATION; STEREOCHEMISTRY; SYNTHESIS;

ALKALOIDS; ALLYL COMPOUNDS; AZIRIDINES; CATALYSIS; MODELS, CHEMICAL; NUPHAR; PALLADIUM; PIPERIDINES; QUINOLIZINES; STEREOISOMERISM;

EID: 0344824459     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035156t     Document Type: Article

References (20)

1. For leading references on isolation studies and bioactivities see: (a) Miyazawa, M.; Yoshio, K.; Ishikawa, Y.; Kameoka, H. J. Agric. Food Chem. 1998, 46, 1059. (b) Matsuda, M.; Shimoda, H.; Yoshikawa, M. Bioorg. Med. Chem. Lett. 2001, 9, 1031.
2. For leading references on isolation studies and bioactivities see: (a) Miyazawa, M.; Yoshio, K.; Ishikawa, Y.; Kameoka, H. J. Agric. Food Chem. 1998, 46, 1059. (b) Matsuda, M.; Shimoda, H.; Yoshikawa, M. Bioorg. Med. Chem. Lett. 2001, 9, 1031.
3. (a) Hwang, Y. C.; Fowler, F. W. J. Org. Chem. 1985, 50, 2719.
4. (b) Hwang, Y. C.; Chu, M.; Fowler, F. W. J. Org. Chem. 1985, 50, 3885.
5. Bohlmann, F.; Winterfeldt, E.; Laurent, H.; Ude, W. Tetrahedron 1963, 19, 195.
6. (a) Natsume, M.; Ogawa, M. Heterocycles 1981, 15, 237.
7. (b) LaLonde, R. T.; Muhammad, N.; Wong, C. F.; Sturiale, E. R. J. Org. Chem. 1980, 45, 3664.
8. (a) Hedley, S. J.; Moran, W. J.; Prenzel, A. H. G. P.; Price, D. A.; Harrity, J. P. A. Synlett 2001, 1596.
9. (b) Hedley, S. J.; Moran, W. J.; Price, D. A.; Harrity, J. P. A. J. Org. Chem. 2003, 68, 4286.
10. (c) Recently, a complementary [3 + 3] cycloaddition approach to piperidines has been reported: Slkenicka, H. M.; Hsung, R. P.; McLaughlin, M. J.; Wei, L.-I.; Gerasyuto, A. I.; Brennessel, W. B. J. Am. Chem. Soc. 2002, 124, 10435.
11. Trost and co-workers have pioneered the use of Pd-TMM complexes in cycloaddition reactions: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1 and references therein.
12. Berry, M. B.; Craig, D. Synlett 1992, 41.
13. (a) Hanessian, S.; Vanasse, B. Can. J. Chem. 1993, 71, 1401.
14. (b) Humphrey, J. M.; Bridges, R. J.; Hart, J. A.; Chamberlin, A. R. J. Org. Chem. 1994, 59, 2467.
15. (c) Wang, J.; Hou, Y.; Wu, P.; Qu, Z.; Chan, A. S. C. Tetrahedron: Asymmetry 1999, 10, 4553.
16. (9) Crystallographic data for 8 has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 210220. Copies of these data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
17. (10) We have investigated a number of phosphine and phosphite ligands in an attempt to promote this transformation and DPPP has been optimum thus far. For example the use of triisopropyl phosphite resulted in very low conversion (furnishing 11 in 10-15% yield) whereas tributylphosphine generated 12 in > 70% yield. A full account of our efforts to promote the Pd-catalysed [3 + 3] cycloaddition reaction will be presented elsewhere.
18. 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.
19. 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.
20. Trost, B. M.; Chan, D. M. T.; Nanninga, T. N. Org. Synth. 1984, 62, 58.