Efficient total synthesis of (+)-dihydropinidine, (-)-epidihydropinidine, and (-)-pinidinone

Journal of Natural Products

Volumn 74, Issue 4, 2011, Pages 803-808

  Kavala, Miroslav ^a   Mathia, František ^a   Kožíšek, Jozef ^a   Szolcsányi, Peter ^a  

^a SLOVAK UNIVERSITY OF TECHNOLOGY   (Slovakia)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; DIHYDROPINIDINE; EPICHLOROHYDRIN; EPIDIHYDROPINIDINE; PINIDINONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CRYSTALLOGRAPHY; OXIDATION; REDUCTION; STEREOCHEMISTRY; SYNTHESIS; X RAY ANALYSIS;

ALKALOIDS; MOLECULAR STRUCTURE; PICEA; PINUS; PIPERIDINES; STEREOISOMERISM;

EID: 79955390359     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np100852p     Document Type: Article

References (44)

1. Schneider, M. J.; Montali, J. A.; Hazen, D.; Stanton, C. E. J. Nat. Prod. 1991, 54, 905-909
2. Tawara, J. N.; Blokhin, A.; Foderaro, T. A.; Stermitz, F. R.; Hope, H. J. Org. Chem. 1993, 58, 4813-4818
3. Brown, W. V.; Moore, B. P. Aust. J. Chem. 1982, 35, 1255-1261
4. Attygalle, A. B.; Xu, S.-Ch.; McCormick, K. D.; Meinwald, J. Tetrahedron 1993, 49, 9333-9342
5. Shtykova, L.; Masuda, M.; Eriksson, C.; Sjödin, K.; Marling, E.; Schlyter, F.; Nydén, M. Prog. Org. Coat. 2008, 63, 160-166
6. Husson, H.-P. J. Nat. Prod. 1985, 48, 894-906
7. Lu, Z.-H.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1993, 593-596
8. Cheìnevert, R.; Dickman, M. J. Org. Chem. 1996, 61, 3332-3341
9. Davis, F. A.; Szewczyk, J. M. Tetrahedron Lett. 1998, 39, 5951-5954
10. Yamauchi, T.; Fujikura, H.; Higashiyama, K.; Takahashi, H.; Ohmiya, S. J. Chem. Soc., Perkin Trans. 1 1999, 2791-2794
11. Ciblat, S.; Besse, P.; Papastergiou, V.; Veschambre, H.; Canet, J.-L.; Troin, Y. Tetrahedron: Asymmetry 2000, 11, 2221-2229
12. Fréville, S.; Delbecq, P.; Thuy, V. M.; Petit, H.; Célérier, J. P.; Lhommet, G. Tetrahedron Lett. 2001, 42, 4609-4611
13. Amat, M.; Llor, N.; Hidalgo, J.; Escolano, C.; Bosch, J. J. Org. Chem. 2003, 68, 1919-1928
14. Yamauchi, S.; Mori, S.; Hirai, Y.; Kinoshita, Y. Biosci. Biotechnol. Biochem. 2004, 68, 676-684
15. Kranke, B.; Hebrault, D.; Schultz-Kukula, M.; Kunz, H. Synlett 2004, 671-674
16. Kranke, B.; Kunz, H. Can. J. Chem. 2006, 84, 625-641
17. Eriksson, C.; Sjödin, K.; Schlyter, F.; Högberg, H.-E. Tetrahedron: Asymmetry 2006, 17, 1074-1080
18. González-Gómez, J. C.; Foubelo, F.; Yus, M. Synlett 2008, 2777-2780
19. Passarella, D.; Riva, S.; Grieco, G.; Cavallo, F.; Checa, B.; Arioli, F.; Riva, E.; Comi, D.; Danieli, B. Tetrahedron: Asymmetry 2009, 20, 192-197
20. Kubizna, P.; špánik, I.; Kožíšek, J.; Szolcsányi, P. Tetrahedron 2010, 66, 2351-2355
21. Taber, D. F.; Deker, P. B. J. Org. Chem. 1988, 53, 2968-2971
22. Dinh, T. Q.; Du, X.; Smith, Ch. D.; Armstrong, R. W. J. Org. Chem. 1997, 62, 6773-6783
23. Selected reviews on Wacker-Tsuji oxidation: Smidt, J.; Sieber, R. Angew. Chem., Int. Ed. Engl. 1962, 1, 80-88
24. Tsuji, J. Synthesis 1984, 369-383
25. Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecule; University Science Books, 1994; pp 199 - 208.
26. Feringa, B. L. Wacker Oxidation. In Transition Metals in Organic Synthesis; Beller, M.; Bolm, C., Eds.; Wiley-VCH, 1998; Vol. 2, pp 307 - 315.
27. Hintermann, L. Wacker-Type Oxidations. In Transition Metals in Organic Synthesis, 2nd ed.; Beller, M.; Bolm, C., Eds.; Wiley-VCH, 2004; Vol. 2, pp 379 - 388.
28. Cornell, C. N.; Sigman, M. S. Inorg. Chem. 2007, 46, 1903-1909
29. Li, J. J. Wacker-Tsuji Oxidation. In Name Reactions for Functional Group Transformations; Li, J.; Corey, E. J., Eds.; John Wiley & Sons, 2007; pp 309 - 326.
30. While the Wacker-Tsuji oxidation of azidoalkenes is previously unknown, analogous transformation of corresponding alkenyl amines was described. However, the terminal double bond of such substrates tends to isomerize under the applied catalytic conditions, resulting in a complex mixture of amino ketones and/or cyclic imines as final products. Pugin, B.; Venanzi, M. L. J. Am. Chem. Soc. 1983, 105, 6877-6881
31. Tsuji, J.; Nagashima, H.; Nemoto, H. Org. Synth., Coll. Vol. 7 1990, 137 - 139.
32. Cornell, C. N.; Sigman, M. S. Org. Lett. 2006, 8, 4117-4120
33. Kulkarni, M. G.; Bagale, S. M.; Shinde, M. P.; Gaikwad, D. D.; Borhade, A. S.; Dhondge, A. P.; Chavhan, S. W.; Shaikh, Y. B.; Ningdale, V. B.; Desai, M. P.; Birhade, D. R. Tetrahedron Lett. 2009, 50, 2893-2894
34. Wang, G.-W.; Yuan, T.-T. J. Org. Chem. 2010, 75, 476-479
35. Mitsudome, T.; Umetani, T.; Nosaka, N.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Angew. Chem., Int. Ed. 2006, 45, 481-485
36. Mitsudome, T.; Mizumoto, K.; Mizugaki, T.; Jitsukawa, K.; Kaneda, K. Angew. Chem., Int. Ed. 2010, 49, 1238-1240
37. Langer, P.; Freifeld, I.; Shojaei, H. Chem. Commun. 2003, 3044-3045
38. Matsumura, Y.; Maruoka, K.; Yamamoto, H. Tetrahedron Lett. 1982, 23, 1929-1932
39. Maruoka, K.; Miyazaki, T.; Ando, M.; Matsumura, Y.; Sakane, S.; Hattori, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 2831-2843
40. Yamaguchi, R.; Nakazono, Y.; Matsuki, T.; Hata, E.; Kawanisi, M. Bull. Chem. Soc. Jpn. 1987, 60, 215-222
41. For X-ray measurement details and structure determination of 2 see Supporting Information. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC- 800711. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: (internat.) + 44 1223/336-033; e-mail: deposit@ccdc.cam.ac.uk ].
42. Enders, D.; Jegelka, U. Synlett 1992, 999-1002
43. Kumar, P.; Gupta, P. Synlett 2009, 1367-1382
44. Munchof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400