A highly regioselective, protecting group controlled, synthesis of bicyclic compounds via Pd-catalysed intramolecular cyclisations

Tetrahedron Letters

Volumn 54, Issue 18, 2013, Pages 2243-2246

  Tasic, Gordana ^a   Randjelovic, Jelena ^a   Vusurovic, Nikola ^a   Maslak, Veselin ^b   Husinec, Suren ^c   Savic, Vladimir ^a  

^a UNIVERSITY OF BELGRADE   (Serbia)

^b UNIVERSITY OF BELGRADE   (Serbia)

^c Institute for Chemistry   (Serbia)

Author keywords

Bicyclic compounds; Corialstonidine; Corialstonine; Heck reaction; Regioselectivity

Indexed keywords

ALKALOID DERIVATIVE; ALLYL ALCOHOL; CORIALSTONIDINE; CORIALSTONINE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; HECK REACTION; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; TAUTOMERIZATION;

EID: 84875719109     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.02.068     Document Type: Article

References (32)

1. A. Cherif, G. Massiot, and L. Le Men-Olivier Heterocycles 26 1987 3055 3058
2. C.W. Wright, D. Alle, J.D. Phillipson, G.C. Kirby, D.C. Warhurst, G. Massiot, and L. Le Men-Olivier J. Ethnopharmacol. 40 1993 41 45
3. Various concepts of regioselective transformations have been reviewed, see: J. Mahatthananchai, A.M. Dumas, and J.W. Bode Angew. Chem., Int. Ed. 51 2012 10954 10990
4. G. Rousseau, and B. Breit Angew. Chem., Int. Ed. 50 2011 2450 2494
5. For reviews, see: J. Muzart Tetrahedron 61 2005 4179 4212
6. J. Ruan, and J. Xiao Acc. Chem. Res. 44 2011 614 626
7. For some recent examples, see: D. Brandt, V. Bellosta, J. Cossy, and J. Panther Org. Lett. 14 2012 5594 5597
8. A. Rohrich, and T.J.J. Müller ARKIVOC iii 2012 297 311
9. P. Colbon, J. Ruan, M. Purdie, K. Mulholland, and J. Xiao Org. Lett. 13 2011 5456 5459
10. M.T. Stone Org. Lett. 13 2011 2326 2329
11. B. Schmidt, F. Holter, A. Kelling, and U. Schilde J. Org. Chem. 76 2011 3357 3365
12. J. Liu, J. Zhu, H. Jiang, W. Wang, and J. Li Chem. Commun. 46 2010 415 417
13. E. Alacid, and C. Najera Adv. Synth. Catal. 349 2007 2572 2584
14. V. Calo, A. Nacci, A. Monopoli, and V. Ferola J. Org. Chem. 72 2007 2596 2601
15. J. Mo, L. Xu, J. Ruan, S. Liu, and J. Xiao Chem. Commun. 2006 3591 3593
16. J.-M. Gaudin Tetrahedron Lett. 32 1991 6113 6116
17. L. Shi, C.K. Narula, K.T. Mak, L. Kao, Y. Xu, and R.F. Heck J. Org. Chem. 48 1983 3894 3900
18. K. Kondo, M. Sodeoka, M. Mori, and M. Shibasaki Tetrahedron Lett. 34 1993 4219 4222
19. K. Kondo, M. Sodeoka, M. Mori, and M. Shibasaki Synthesis 1993 920 930
20. S.A. Kelly, Y. Foricher, J. Mann, and J.M. Bentley Org. Biomol. Chem. 1 2003 2865 2876
21. A.M.C.H. van den Nieuwendijk, A.B.T. Ghisaidoobe, H.S. Overkleeft, J. Brussee, and A. van der Gen Tetrahedron 60 2004 10385 10396
22. E.J. Corey, and A. Venkateswarlu J. Am. Chem. Soc. 94 1972 6190 6191
23. H. Zhao, A. Ariafard, and Z. Lin Organometallics 25 2006 812 819
24. For some examples of anti-hydride elimination in Pd-catalysed reactions, see: M. Lautens, and Y.-Q. Fang Org. Lett. 5 2003 3679 3682
25. K. Maeda, E.J. Farrington, E. Galardon, B.D. John, and J.M. Brown Adv. Synth. Catal. 344 2002 104 109
26. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
27. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785 789
28. S.H. Vosko, L. Wilk, and M. Nusair Can. J. Phys. 58 1980 1200 1211
29. F. Weigend, and R. Alhrichs Phys. Chem. Chem. Phys. 7 2005 3297 3305
30. J.W. McIver, and A.K. Komornicki J. Am. Chem. Soc. 94 1972 2625 2633
31. C. Amatore, E. Came, A. Jutand, M.A. M'Barki, and G. Meyer Organometallics 14 1995 5605 5614
32. A. Jutand M. Oestreich, The Mizoroki-Heck Reaction 2009 Wiley Chichester 1 50