Neat total synthesis of six monoterpenic alkaloids of the actinidine series

Tetrahedron

Volumn 63, Issue 18, 2007, Pages 3702-3706

  Robert, Nicolas ^a   Hoarau, Christophe ^a   Marsais, Francis ^a  

^a Normandie Université   (France)

Author keywords

Intramolecular Heck reaction; Nucleophilic addition; Oxazoline; Pyridine alkaloid; Pyridoterpene

Indexed keywords

3 BROMO 5 (PHENYLOXAZOLIN 2 YL)PYRIDINE; ACTINIDINE; ALKALOID DERIVATIVE; BOSCHNIAKINIC ACID; DEOXYRHEXIFOLINE; INDICAINE; PLANTAGONINE; PYRIDINE DERIVATIVE; TECOSTIDINE; TERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ENANTIOMER; HECK REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 34047167878     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.02.090     Document Type: Article

References (30)

1. Sakan T., Fujino A., Murai F., Butsugan Y., and Suzui A. Bull. Chem. Soc. Jpn. 32 (1959) 315-316
2. Saxena J., and Mathela C.S. Appl. Environ. Microbiol. 62 (1996) 702-704
3. Takamatsu S., Kim Y.-P., Hayashi M., Furuhata K., Takayanagi H., Komiyama K., Woodruff H.B., and Omura S. J. Antibiot. 48 (1995) 1090-1094
4. Komiyama K., Takamatsu S., Kim Y.-P., Matsumoto A., Takahashi Y., Hayashi M., Woodruff H.B., and Omura S. J. Antibiot. 48 (1995) 1086-1089
5. Benkrief R., Skaltsounis A.-L., Tillequin F., Koch M., and Puset J. Planta Med. 57 (1991) 79-80
6. Skaltsounis A.-L., Tillequin F., Koch M., Puset J., and Chauviere G. Planta Med. 55 (1989) 191-192
7. Roby M.R., and Stermitz F.R. J. Nat. Prod. 47 (1984) 846-853
8. McCoy J.W., and Stermitz F.R. J. Nat. Prod. 46 (1983) 902-907
9. Sakan T., Murai F., Hayashi Y., Honda Y., Shono T., Nakajima M., and Kato M. Tetrahedron 23 (1967) 4635-4652
10. Groos D., Berg W., and Schutte H.R. Z. Chem. 13 (1973) 296-297
11. Ripperger H. Pharmazie 34 (1979) 577
12. Costantino L., Raimondi L., Pirisino R., Brunetti T., Pesotto P., Giannessi F., Lins A.P., Barlocco D., Antolini L., and El-Abady S.A. Il Farmaco 58 (2003) 781-785
13. Torssell K. Acta Chem. Scand. 22 (1968) 2715-2741
14. Hammouda Y., and Le Men J. Bull. Chem. Soc. Fr. 12 (1963) 2901-2902
15. Ranarivelo Y., Hotellier F., Skaltsounis A.L., and Tillequin F. Heterocycles 31 (1990) 1727-1731
16. Jones K., Fiumana A., and Escudero-Hernandez M.L. Tetrahedron 56 (2000) 397-406
17. Zhai and co-workers reported first the construction of the cyclopenta[c]pyridine framework via an intramolecular Heck reaction. Zhao J., Yang X., Jia X., Luo S., and Zhai H. Tetrahedron 59 (2003) 9379-9382
18. Chang C.-Y., Liu H.-M., and Chow T.J. J. Org. Chem. 71 (2006) 6302-6304
19. Reviews:
20. Dounay A.B., and Overman L.E. Chem. Rev. 103 (2003) 2945-2963
21. Link J.T. Org. React. 60 (2002) 157-534
22. Braese S., and De Meijere A. In: Negishi E. (Ed). Handbook of Organopalladium Chemistry for Organic Synthesis (2002), Wiley and Sons, Weinheim, Germany 1223-1254
23. Boger D.L., and Turnbull P. J. Org. Chem. 63 (1998) 8004-8011
24. Abelman M.M., Oh T., and Overman L.E. J. Org. Chem. 52 (1987) 4130-4133
25. Karabelas K., Westerlund C., and Hallberg A. J. Org. Chem. 50 (1985) 3896-3900
26. 16c (c 1.00, MeOH);
27. Hammouda Y., Plat M., and Le Men J. Ann. Pharm. Fr. 21 (1963) 699-702
28. Torsell K., and Wahlberg K. Acta Chem. Scand. 21 (1967) 53-62
29. Cavill G.W.K., and Zeitlin A. Aust. J. Chem. 20 (1967) 349-357
30. Hammouda Y., and Le Men J. Bull. Chem. Soc. Chim. Fr. (1963) 2901-2902