Development of novel Lewis acid catalyzed cycloisomerizations: Synthesis of bicyclo[3.1.0]hexenes and cyclopentenones

Tetrahedron

Volumn 59, Issue 45, 2003, Pages 8919-8930

  Miller, Aubry K ^a   Banghart, Matthew R ^a   Beaudry, Christopher M ^a   Suh, Judy M ^a   Trauner, Dirk ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Cycloisomerization; Lewis acid; Molluscan polypropionate

Indexed keywords

BICYCLO COMPOUND; CYCLOPENTENONE DERIVATIVE; KETONE DERIVATIVE; LEWIS ACID;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CYCLIZATION; INFRARED SPECTROSCOPY; ISOMERISM; MASS SPECTROMETRY; MOLLUSC; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 0142217509     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.04.006     Document Type: Article

References (34)

1. Okamura W.H., De Lera A.R. Trost B. Comprehensive Organic Synthesis. Vol. 5:1991;699 ff Pergamon, Oxford.
2. Woodward R.B., Hoffmann R. The Conservation of Orbital Symmetry. 1970;VCH, Weinheim.
3. For examples see: (a) Nicolaou K.C., Sorensen E.J. Classics in Total Synthesis. 1996;VCH, Weinheim. p 265; and references cited therein (endiandric acids) (b) Beaudry C.M., Trauner D. Org. Lett. 4:2002;2221. (SNF4435C and D) (c) Lee J.C., Strobel G.A., Lobkovsky E., Clardy J. J. Org. Chem. 61:1996;3232. torreyanic acid.
4. For examples see: (a) Nicolaou K.C., Sorensen E.J. Classics in Total Synthesis. 1996;VCH, Weinheim. p 265; and references cited therein (endiandric acids) (b) Beaudry C.M., Trauner D. Org. Lett. 4:2002;2221. (SNF4435C and D) (c) Lee J.C., Strobel G.A., Lobkovsky E., Clardy J. J. Org. Chem. 61:1996;3232. torreyanic acid.
5. For examples see: (a) Nicolaou K.C., Sorensen E.J. Classics in Total Synthesis. 1996;VCH, Weinheim. p 265; and references cited therein (endiandric acids) (b) Beaudry C.M., Trauner D. Org. Lett. 4:2002;2221. (SNF4435C and D) (c) Lee J.C., Strobel G.A., Lobkovsky E., Clardy J. J. Org. Chem. 61:1996;3232. torreyanic acid.
6. (a) Padwa A., Brodsky L., Clough C. J. Am. Chem. Soc. 94:1972;6767 (b) Dauben W.G., Smith J.H. J. Org. Chem. 32:1967;3244 (c) Dauben W.G., Kellogg M.S., Seemann J.I., Vietmeyer N.D., Wendschuk P.H. Pure Appl. Chem. 33:1973;197 (d) Barton D.H.R., Kende A.S. J. Chem. Soc. 1958;688 (e) George M.V., Mitra A., Sukumaran K.B. Angew. Chem. Int. Ed. 19:1980;973.
7. (a) Padwa A., Brodsky L., Clough C. J. Am. Chem. Soc. 94:1972;6767 (b) Dauben W.G., Smith J.H. J. Org. Chem. 32:1967;3244 (c) Dauben W.G., Kellogg M.S., Seemann J.I., Vietmeyer N.D., Wendschuk P.H. Pure Appl. Chem. 33:1973;197 (d) Barton D.H.R., Kende A.S. J. Chem. Soc. 1958;688 (e) George M.V., Mitra A., Sukumaran K.B. Angew. Chem. Int. Ed. 19:1980;973.
8. (a) Padwa A., Brodsky L., Clough C. J. Am. Chem. Soc. 94:1972;6767 (b) Dauben W.G., Smith J.H. J. Org. Chem. 32:1967;3244 (c) Dauben W.G., Kellogg M.S., Seemann J.I., Vietmeyer N.D., Wendschuk P.H. Pure Appl. Chem. 33:1973;197 (d) Barton D.H.R., Kende A.S. J. Chem. Soc. 1958;688 (e) George M.V., Mitra A., Sukumaran K.B. Angew. Chem. Int. Ed. 19:1980;973.
9. (a) Padwa A., Brodsky L., Clough C. J. Am. Chem. Soc. 94:1972;6767 (b) Dauben W.G., Smith J.H. J. Org. Chem. 32:1967;3244 (c) Dauben W.G., Kellogg M.S., Seemann J.I., Vietmeyer N.D., Wendschuk P.H. Pure Appl. Chem. 33:1973;197 (d) Barton D.H.R., Kende A.S. J. Chem. Soc. 1958;688 (e) George M.V., Mitra A., Sukumaran K.B. Angew. Chem. Int. Ed. 19:1980;973.
10. (a) Padwa A., Brodsky L., Clough C. J. Am. Chem. Soc. 94:1972;6767 (b) Dauben W.G., Smith J.H. J. Org. Chem. 32:1967;3244 (c) Dauben W.G., Kellogg M.S., Seemann J.I., Vietmeyer N.D., Wendschuk P.H. Pure Appl. Chem. 33:1973;197 (d) Barton D.H.R., Kende A.S. J. Chem. Soc. 1958;688 (e) George M.V., Mitra A., Sukumaran K.B. Angew. Chem. Int. Ed. 19:1980;973.
11. Okamura W.H., De Lera A.R. Trost B. Comprehensive Organic Synthesis. Vol. 5:1991;79 f Pergamon, Oxford.
12. Criegee R., Askani R. Angew. Chem. Int. Ed. 7:1968;537.
13. Miller A.K., Trauner D. Angew. Chem. Int. Ed. 42:2003;549.
14. Ojima I. Comprehensive Asymmetric Catalysis. 2000;Wiley, New York.
15. (a) Cimino G., Fontana A., Gavagnin M. Curr. Org. Chem. 3:1999;327 (b) Davies-Coleman M.T., Garson M.J. Nat. Prod. Rep. 15:1998;477.
16. (a) Cimino G., Fontana A., Gavagnin M. Curr. Org. Chem. 3:1999;327 (b) Davies-Coleman M.T., Garson M.J. Nat. Prod. Rep. 15:1998;477.
17. (a) Ireland C., Faulkner D.J., Solheim B.A., Clardy J. J. Am. Chem. Soc. 100:1978;1002 (b) Ireland C., Scheuer P.J. Science. 205:1979;922 (c) Gavagnin M., Spinella A., Castelluccio F., Cimino G.J. Nat. Prod. 57:1994;298 (d) Ireland C., Faulkner D.J. Tetrahedron. 37:(Suppl. 1):1981;233 (e) Ksebati M.B., Schmitz F.J. J. Org. Chem. 50:1985;5637.
18. (a) Ireland C., Faulkner D.J., Solheim B.A., Clardy J. J. Am. Chem. Soc. 100:1978;1002 (b) Ireland C., Scheuer P.J. Science. 205:1979;922 (c) Gavagnin M., Spinella A., Castelluccio F., Cimino G.J. Nat. Prod. 57:1994;298 (d) Ireland C., Faulkner D.J. Tetrahedron. 37:(Suppl. 1):1981;233 (e) Ksebati M.B., Schmitz F.J. J. Org. Chem. 50:1985;5637.
19. (a) Ireland C., Faulkner D.J., Solheim B.A., Clardy J. J. Am. Chem. Soc. 100:1978;1002 (b) Ireland C., Scheuer P.J. Science. 205:1979;922 (c) Gavagnin M., Spinella A., Castelluccio F., Cimino G.J. Nat. Prod. 57:1994;298 (d) Ireland C., Faulkner D.J. Tetrahedron. 37:(Suppl. 1):1981;233 (e) Ksebati M.B., Schmitz F.J. J. Org. Chem. 50:1985;5637.
20. (a) Ireland C., Faulkner D.J., Solheim B.A., Clardy J. J. Am. Chem. Soc. 100:1978;1002 (b) Ireland C., Scheuer P.J. Science. 205:1979;922 (c) Gavagnin M., Spinella A., Castelluccio F., Cimino G.J. Nat. Prod. 57:1994;298 (d) Ireland C., Faulkner D.J. Tetrahedron. 37:(Suppl. 1):1981;233 (e) Ksebati M.B., Schmitz F.J. J. Org. Chem. 50:1985;5637.
21. (a) Ireland C., Faulkner D.J., Solheim B.A., Clardy J. J. Am. Chem. Soc. 100:1978;1002 (b) Ireland C., Scheuer P.J. Science. 205:1979;922 (c) Gavagnin M., Spinella A., Castelluccio F., Cimino G.J. Nat. Prod. 57:1994;298 (d) Ireland C., Faulkner D.J. Tetrahedron. 37:(Suppl. 1):1981;233 (e) Ksebati M.B., Schmitz F.J. J. Org. Chem. 50:1985;5637.
22. Dahmann G., Hoffmann R.W. Liebigs Ann. Chem. 1994;837.
23. Still W.C., Gennari C. Tetrahedron Lett. 24:1983;4405.
24. Williams J.M., Jobsen R.B., Yasuda N., Marchesini G., Dolling U.H., Grabowski E.J.J. Tetrahedron Lett. 36:1995;5461.
25. Garey D., Ramirez M.L., Gonzales S., Wertsching A., Tith S., Keefe K., Pena M.R. J. Org. Chem. 61:1996;4853.
26. (a) Oppolzer W., Moretti R., Bernardinelli G. Tetrahedron Lett. 27:1986;4713 (b) Birkbeck A.A., Enders D. Tetrahedron Lett. 39:1998;7823.
27. (a) Oppolzer W., Moretti R., Bernardinelli G. Tetrahedron Lett. 27:1986;4713 (b) Birkbeck A.A., Enders D. Tetrahedron Lett. 39:1998;7823.
28. Beak P., Lee J.K., McKinnie B.G. J. Org. Chem. 43:1978;1367.
29. Moses J.E., Baldwin J.E., Marquez R., Adlington R.M., Claridge T.D.W., Odell B. Org. Lett. 5:2003;661.
30. Habermas K.L., Denmark S.E., Jones T.K. Org. React. 45:1994;1.
31. For related cyclizations that presumably proceed through pentadienal intermediates see (a) Ogawa H., Taketugu Y., Imoto T., Taniguchi Y., Kato H. Tetrahedron Lett. 20:1979;3457 (b) Padwa A., Au A., Lee G.A., Owens W. J. Org. Chem. 40:1975;1142.
32. For related cyclizations that presumably proceed through pentadienal intermediates see (a) Ogawa H., Taketugu Y., Imoto T., Taniguchi Y., Kato H. Tetrahedron Lett. 20:1979;3457 (b) Padwa A., Au A., Lee G.A., Owens W. J. Org. Chem. 40:1975;1142.
33. Takahashi T., Xi Z., Nishihara Y., Huo S., Kasai K., Aoyagi K., Denisov V., Negishi E.-I. Tetrahedron. 53:1997;9123.
34. Petroski R.J., Weisleder D. Synth. Commun. 31:2001;89.