New reactions and step economy: the total synthesis of (±)-salsolene oxide based on the type II transition metal-catalyzed intramolecular [4+4] cycloaddition

Tetrahedron

Volumn 62, Issue 32, 2006, Pages 7505-7511

  Wender, Paul A ^a   Croatt, Mitchell P ^a   Witulski, Bernhard ^b  

^a STANFORD UNIVERSITY   (United States)

^b JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; CYCLOOCTADIENE; NICKEL; OXIDE; SALSOLENE OXIDE; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; ECONOMIC ASPECT; GEOMETRY; ISOMER; MOLECULAR INTERACTION; PRIORITY JOURNAL; SUBSTITUTION REACTION; SYNTHESIS;

EID: 33745353059     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.02.085     Document Type: Article

References (45)

1. Wender P.A., Bi F.C., Gamber G.G., Gosselin F., Hubbard R.D., Scanio M.J.C., Sun R., Williams T.J., and Zhang L. Pure Appl. Chem. 74 (2002) 25-31
2. Wender P.A., Handy S.T., and Wright D.L. Chem. Ind. (London) (1997) 765-769
3. Wender P.A., and Miller B.L. In: Hudlicky T. (Ed). Organic Synthesis: Theory and Applications Vol. 2 (1993), JAI, Greenwich 27-66
4. For a compelling example of step economy through new reactions, see:. Wender P.A., and Ternansky R.J. Tetrahedron Lett. 26 (1985) 2625-2628
5. For discussions of complexity and connectivity analyses, see:. Barone R., and Chanon M. Tetrahedron 61 (2005) 8916-8923
6. Chanon M., Barone R., Baralotto C., Julliard M., and Hendrickson J.B. Synthesis (1998) 1559-1583
7. Bertz S.H., and Sommer T.J. Chem. Commun. (1997) 2409-2410
8. Ref. 1c.
9. For the first metal-catalyzed intramolecular [4+2] reaction, see:. Wender P.A., and Jenkins T.E. J. Am. Chem. Soc. 111 (1989) 6432-6434
10. For the first metal-catalyzed intramolecular [5+2] reaction, see:. Wender P.A., Takahashi H., and Witulski B. J. Am. Chem. Soc. 117 (1995) 4720-4721
11. For the first metal-catalyzed intermolecular [5+2] reaction, see:. Wender P.A., Rieck H., and Fuji M. J. Am. Chem. Soc. 120 (1998) 10976-10977
12. For the first [5+2+1] reaction, see:. Wender P.A., Gamber G.G., Hubbard R.D., and Zhang L. J. Am. Chem. Soc. 124 (2002) 2876-2877
13. For the first [5+2+1] reaction using allenes, see:. Wegner H.A., de Meijere A., and Wender P.A. J. Am. Chem. Soc. 127 (2005) 6530-6531
14. For the first report of a diene-yne [4+2+1] and dienyl Pauson-Khand reaction, see:. Wender P.A., Deschamps N.M., and Gamber G.G. Angew. Chem., Int. Ed. 42 (2003) 1853-1857
15. For the first intermolecular dienyl Pauson-Khand reaction, see:. Wender P.A., Deschamps N.M., and Williams T.J. Angew. Chem., Int. Ed. 43 (2004) 3076-3079
16. For the first report of a diene-ene [2+2+1], see:. Wender P.A., Croatt M.P., and Deschamps N.M. J. Am. Chem. Soc. 126 (2004) 5948-5949
17. For the first [5+1+2+1] reaction, see:. Wender P.A., Gamber G.G., Hubbard R.D., Pham S.M., and Zhang L. J. Am. Chem. Soc. 127 (2005) 2836-2837
18. Reppe W., Schlichting O., Klager K., and Toepel T. Justus Liebigs Ann. Chem. 560 (1948) 1-92
19. Reed H.W.B. J. Chem. Soc. (1954) 1931-1941
20. Wilke G. Angew. Chem., Int. Ed. Engl. 2 (1963) 105-115
21. For reviews, see:
22. Jolly P.W. In: Wilkinson G., Stone F.G.A., and Abel E.W. (Eds). Comprehensive Organometallic Chemistry Vol. 8 (1982), Pergamon, New York, NY 671-711
23. Keim W., Behr A., and Roper M. In: Wilkinson G., Stone F.G.A., and Abel E.W. (Eds). Comprehensive Organometallic Chemistry (1982), Pergamon, New York, NY 371-461
24. Jolly P.W., and Wilke G. The Organic Chemistry of Nickel Vol. 1 (1974), Academic, New York, NY 1-518
25. Jolly P.W., and Wilke G. The Organic Chemistry of Nickel Vol. 2 (1975), Academic, New York, NY 1-416
26. Heimbach P., Jolly P.W., and Wilke G. In: Stone F.G.A., and West R. (Eds). Advances in Organometallic Chemistry Vol. 8 (1970), Academic, New York, NY 29-86
27. Wender P.A., and Ihle N.C. J. Am. Chem. Soc. 108 (1986) 4678-4679
28. Murakami M., Itami K., and Ito Y. Synlett (1999) 951-953
29. Lee P.H., and Lee K. Angew. Chem., Int. Ed. 44 (2005) 3253-3256
30. Takahashi T., Sun W.-H., Liu Y., Nakajima K., and Kotora M. Organometallics 17 (1998) 3841-3843
31. Wender P.A., and Snapper M.L. Tetrahedron Lett. 28 (1987) 2221-2224
32. Wender P.A., Ihle N.C., and Correia C.R.D. J. Am. Chem. Soc. 110 (1988) 5904-5906
33. Mehta G., and Singh V. Chem. Rev. 99 (1999) 881-930
34. Wender P.A., and Tebbe M.J. Synthesis 12 (1991) 1089-1094
35. Weyerstahl P., Marschall H., Wahlburg H.-C., and Kaul V.K. Liebigs Ann. Chem. (1991) 1353-1355
36. Paquette L.A., Sun L.-Q., Watson T.J.N., Friedrich D., and Freeman B.T. J. Am. Chem. Soc. 119 (1997) 2767-2768
37. Paquette L.A., Sun L.-Q., Watson T.J.N., Friedrich D., and Freeman B.T. J. Org. Chem. 62 (1997) 8155-8161
38. Barberis F., Barone R., Arbelot M., Baldy A., and Chanon M. J. Chem. Inf. Comput. Sci. 35 (1995) 467-471
39. See Ref. 2a.
40. Büchi G., and Wüest H. Helv. Chim. Acta 50 (1967) 2440-2445
41. Umbreit M.A., and Sharpless K.B. J. Am. Chem. Soc. 99 (1977) 5526-5528
42. For a review, see:. Chai Y., Hong S., Lindsay H.A., McFarland C., and McIntosh M.C. Tetrahedron 58 (2002) 2905-2928
43. Wender P.A., and Smith T.E. J. Org. Chem. 60 (1995) 2962-2963
44. Wender P.A., and Smith T.E. Tetrahedron 54 (1998) 1255-1275
45. BORSM yield is based on recovered starting material.