Pd-catalyzed cross-coupling of allylsilane-vinylcopper species with aryl and vinyl halides: the first total synthesis of (-)-nomadone

Tetrahedron

Volumn 65, Issue 28, 2009, Pages 5535-5540

  Pulido, Francisco J ^a   Barbero, Asunción ^a   García, Carlos ^a  

^a UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALLENE DERIVATIVE; CITRONELLAL; COPPER DERIVATIVE; HALIDE; IPSDIENOL; IPSENOL; NOMADONE; PALLADIUM; SESQUITERPENE DERIVATIVE; SILANE DERIVATIVE; TERPENE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; BEETLE; CATALYSIS; CATALYST; CROSS COUPLING REACTION; PRIORITY JOURNAL; SYNTHESIS; TEMPERATURE;

APOIDEA; IPS PARACONFUSUS; NOMADA; SCOLYTINAE;

EID: 66349120415     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.01.118     Document Type: Article

References (58)

1. Lhermitte H., and Grierson D.S. Contemp. Org. Synth. 3 (1996) 41-63 and 93-124
2. Beau J.M. In: Lucaks G., and Ohno M. (Eds). Polyene Macrolides: Stereostructural Elucidation and Synthetic Studies of a few Members in Recent Progress in the Chemical Synthesis of Antibiotics (1990), Springer, Berlin, Heidelberg 135
3. Rychnovsky S.D. Chem. Rev. 95 (1995) 2021-2040
4. In: de Meijere A., and Diederich F. (Eds). Metal-Catalyzed Cross-coupling Reactions. 2nd ed. (2004), Wiley-VCH, Weinheim
5. Hegedus L.S. Transition Metals in the Synthesis of Complex Organic Molecules. 2nd ed. (1999), University Science Books, Sausalito, CA
6. Knight D.W. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 3 (1991), Pergamon, New York, NY 481-520
7. Sonogashira K. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 3 (1991), Pergamon, New York, NY 521-549
8. In: Negishi E.I. (Ed). Handbook of Organopalladium Chemistry for Organic Synthesis (2002), Wiley Interscience, New York, NY
9. Nicolau K.C., Bulger P.G., and Sarlah D. Angew. Chem., Int. Ed. 44 (2005) 4442-4489
10. Negishi E.I. J. Organomet. Chem. 653 (2002) 34-40
11. Tsuji J. Palladium Reagents and Catalysts (2004), Wiley-VCH, Chichester, UK
12. Negishi E.I. In: Knochel P., and Jones P. (Eds). Organozinc Reagents (1999), Oxford University Press, Oxford, UK Chapter 11
13. Erdik E. Tetrahedron 48 (1992) 9577-9648
14. Hegedus L.S. J. Organomet. Chem. 392 (1990) 285-608
15. Hegedus L.S. J. Organomet. Chem. 380 (1990) 169-428
16. Hegedus L.S. J. Organomet. Chem. 360 (1989) 409-635
17. Tamao K. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 3 (1991), Pergamon, New York, NY 435
18. Murahashi S.I. J. Organomet. Chem. 653 (2002) 27-33
19. Suzuki A. J. Organomet. Chem. 576 (1999) 147-168
20. Miyaura N., and Suzuki A. Chem. Rev. 95 (1995) 2457-2483
21. Davies A.G. Organotin Chemistry. 2nd ed. (2004), Wiley-VCH, New York, NY
22. Farina V., Krishnamurthy V., and Scott W.J. The Stille Reaction (1998), Wiley-VCH, New York, NY
23. Stille J.K. Angew. Chem., Int. Ed. Engl. 25 (1986) 508-524
24. Horn K.A. Chem. Rev. 95 (1995) 1317-1350
25. Jabri N., Alexakis A., and Normant J.F. Tetrahedron Lett. 22 (1981) 959-962
26. Jabri N., Alexakis A., and Normant J.F. Tetrahedron Lett. 23 (1982) 1589-1592
27. Jabri N., Alexakis A., and Normant J.F. Bull. Soc. Chim. Fr. (1983) 321-331 and 332-338
28. Gardette M., Jabri N., Alexakis A., and Normant J.F. Tetrahedron 40 (1984) 2741-2750
29. Langkopf E., and Schinzer D. Chem. Rev. 95 (1995) 1375-1408
30. Fleming I., Barbero A., and Walter D. Chem. Rev. 97 (1997) 2063-2192
31. Roush W.R. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 2 (1991), Pergamon, New York, NY 563-593
32. Barbero A., and Pulido F.J. Acc. Chem. Res. 37 (2004) 817-825
33. Barbero A., and Pulido F.J. Chem. Soc. Rev. 34 (2005) 913-920
34. Barbero A., and Pulido F.J. Synthesis (2004) 779-785
35. Barbero A., García C., and Pulido F.J. Tetrahedron Lett. 40 (1999) 6649-6652 and
36. Tetrahedron 56 (2000) 2739-2751
37. Barbero A., Castreño P., García C., and Pulido F.J. J. Org. Chem. 66 (2001) 7723-7728
38. Barbero A., Castreño P., and Pulido F.J. Org. Lett. 5 (2003) 4045-4048
39. Barbero A., Blanco Y., and Pulido F.J. Chem. Commun. (2001) 7723-7728 and
40. J. Org. Chem. 70 (2005) 6876-6883
41. Barbero A., Castreño P., and Pulido F.J. J. Am. Chem. Soc. 127 (2005) 8022-8023
42. Barbero A., García C., and Pulido F.J. Synlett (2001) 824-826
43. The presence of vinylsilane 6 in the reaction mixture accounts for the reversibility of the silylcupration of allene. See:. Fleming I., Rowley M., Cuadrado P., González-Nogal A.M., and Pulido F.J. Tetrahedron 45 (1989) 413-424
44. Draillard K., Lebreton J., and Villiéras J. Tetrahedron: Asymmetry 10 (1999) 4281-4284
45. Chevtchouk T.A., Isakov V.E., and Kulinkovich O.G. Tetrahedron 55 (1999) 13205-13210
46. Hosomi A., Saito M., and Sakurai H. Tetrahedron Lett. 20 (1979) 429-432
47. Riley R.G., and Silverstein R.M. J. Org. Chem. 39 (1974) 1957-1958
48. Katzenellenbogen J.A., and Lenox R.S. J. Org. Chem. 38 (1973) 326-334
49. Brown H.C., and Randald R.S. Tetrahedron 46 (1990) 4463-4472
50. Franck-Neumann M., Martina D., and Heitz M.P. Tetrahedron Lett. 30 (1989) 6679-6682
51. Mori K., and Takikawa H. Tetrahedron 47 (1991) 2163-2168
52. Mori K. Tetrahedron Lett. 17 (1976) 1609-1612 and
53. Mori K. Tetrahedron Lett. 16 (1975) 2187-2190
54. Francke W., Bartels J., Krohn S., Schulz S., Baader E., Tengo J., and Schneider D. Pure Appl. Chem. 61 (1989) 539-542
55. See also:. Tengo J., and Bergstrom G. Science 196 (1977) 1117-1119
56. Francke W., Krohn S., and Tengo J. J. Chem. Ecol. 17 (1991) 557-566
57. In a recent correspondence with Prof. Francke, he pointed out that his group identified nomadone from a complex mixture of terpenes contained in the cephalic secretion of the bees (GC/MS analysis using an authentic sample of racemic nomadone synthesized in their lab), but the mixture was never separated, nor the natural nomadone isolated.
58. Organ M.G., and Winkle D.D. J. Org. Chem. 62 (1997) 1881-1885