A [4+4] annulation strategy for the synthesis of eight-membered carbocycles based on intramolecular cycloadditions of conjugated enynes

Tetrahedron

Volumn 67, Issue 51, 2011, Pages 9890-9898

  Robinson, Julia M ^a   Tlais, Sami F ^a   Fong, Jennie ^a   Danheiser, Rick L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Conjugated enynes; Cycloaddition; Cyclooctatrienones; Eight membered rings; Electrocyclic ring opening

Indexed keywords

ACID; ALLENE DERIVATIVE; BICYCLO COMPOUND;

ANNULATION REACTION; ARTICLE; CHEMICAL REACTION; CONJUGATION; CYCLOADDITION; ELECTRON TRANSPORT; ISOMERIZATION; PRIORITY JOURNAL; RING OPENING; SYNTHESIS;

EID: 81255134396     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.09.031     Document Type: Article

References (48)

1. For a review, see P. Wessig, and G. Muller Chem. Rev. 108 2008 2051 2063
2. R.L. Danheiser, A.E. Gould, R. Fernandez de la Pradilla, and A.L. Helgason J. Org. Chem. 59 1994 5514 5515
3. M.S.B. Wills, and R.L. Danheiser J. Am. Chem. Soc. 120 1998 9378 9379
4. J.R. Dunetz, and R.L. Danheiser J. Am. Chem. Soc. 127 2005 5776 5777
5. M.E. Hayes, H. Shinokubo, and R.L. Danheiser Org. Lett. 7 2005 3917 3920
6. R.P. Johnson Chem. Rev. 89 1989 1111 1124
7. M. Christl Cyclic Allenes Up to Seven-Membered Rings N. Krause, S.K. Hashmi, Modern Allene Chemistry 2004 Wiley-VCH Weinheim 243 357
8. T. Kawase Cyclic Allenes N. Krause, Science of Synthesis Vol. 44 2007 Thieme Stuttgart 395 449
9. R.P. Johnson, and K.M. Konrad Strained Cyclic Allenes and Cumulenes H. Dodziuk, Strained Hydrocarbons 2009 Wiley-VCH Weinheim 122 146
10. The intermediacy of strained cyclic allenes in these reactions is supported by experimental observations and computational studies. See Refs. 1,2a, and V.P. Ananikov J. Phys. Org. Chem. 14 2001 109 121
11. N.A. Petasis, and M.A. Patane Tetrahedron 48 1992 5757 5821
12. G. Mehta, and V. Singh Chem. Rev. 99 1999 881 930
13. Z. Yu, Y. Wang, and Y. Wang Chem. - Asian J. 5 2010 1072 1088
14. For a review of [4+4] cycloaddition strategies, see S.M. Sieburth, and N.T. Cunard Tetrahedron 52 1996 6251 6282
15. For an earlier [4+4] annulation strategy developed in our laboratory, see: R.L. Danheiser, S.K. Gee, and H. Sard J. Am. Chem. Soc. 104 1982 7670 7672
16. For the construction of eight-membered carbocyclic systems via the [4+4] photocycloaddition of enynes with 2-pyridones, see S. Kulyk, W.G. Dougherty, W.S. Kassel, S.A. Fleming, and S.M. Sieburth Org. Lett. 12 2010 3296 3299
17. Reviewed in E.B. Marvell Thermal Electrocyclic Reactions 1980 Academic New York, NY
18. L.F. Tietze, G. Brasche, and K.M. Gericke Domino Reactions in Organic Synthesis 2006 Wiley-VCH Weinheim
19. L.F. Tietze, and U. Beifuss Angew. Chem., Int. Ed. Engl. 32 1993 131 163
20. R.A. Bunce Tetrahedron 51 1995 13103 13159
21. L.F. Tietze Chem. Rev. 96 1996 115 136
22. For examples of Diels-Alder [4+2] cycloadditions involving cyclobutenones, see
23. T.R. Kelly, and R.W. McNutt Tetrahedron Lett. 16 1975 285 288
24. B. Bienfait, G. Coppe-Motte, R. Merenyi, and H.G. Viehe Tetrahedron 47 1991 8167 8176
25. X. Li, and S.J. Danishefsky J. Am. Chem. Soc. 132 2010 11004 11005
26. H.H. Wasserman, J.U. Piper, and E.V. Dehmlow J. Org. Chem. 38 1973 1451 1455
27. Prepared by Sonogashira coupling of 4-pentyn-1-ol with 2-bromopropene as described by A.K.S. Hashmi, and P. Sinha Adv. Synth. Catal. 346 2004 432 438
28. Hydrolysis of the intermediate vinylogous hemiacetal generated in the organolithium addition to 3-ethoxycyclobutenone was best accomplished using the general protocol of L.S. Liebeskind, and K.R. Wirtz J. Org. Chem. 55 1990 5350 5358
29. Reviewed in R.L. Danheiser, G.B. Dudley, and W.F. Austin Alkenylketenes R.L. Danheiser, Science of Synthesis Vol. 23 2006 Thieme Stuttgart 493 568
30. W. Adam, O. Cueto, and O. De Lucchi Chem. Ber. 115 1982 1170 1177
31. H. Meier, M. Lorch, H. Petersen, and H. Gugel Chem. Ber. 115 1982 1418 1424
32. A.C. Cope, A.C. Haven, F.L. Ramp, and E.R. Trumbull J. Am. Chem. Soc. 74 1952 4867 4871
33. R. Huisgen, G. Boche, A. Dahmen, and W. Hetchl Tetrahedron Lett. 9 1968 5215 5219
34. P.J. Wagner, and K. Nahm J. Am. Chem. Soc. 109 1987 6528 6530
35. T. Fujiwara, T. Ohsaka, T. Inoue, and T. Takeda Tetrahedron Lett. 29 1988 6283 6286
36. Computational study: A. Fry Tetrahedron 64 2008 2101 2103
37. S. Nahm, and S.M. Weinreb Tetrahedron Lett. 22 1981 3815 3818
38. M.P. Sibi Org. Prep. Proceed. Int. 25 1993 15 40
39. S. Balasubramaniam, and I.S. Aidhen Synthesis 2008 3707 3738
40. A. Song, K.A. Parker, and N.S. Sampson J. Am. Chem. Soc. 131 2009 3444 3445
41. 5 under vacuum (0.1 mmHg) for 48 h prior to use
42. L.M. Bishop, J.E. Barbarow, R.G. Bergman, and D. Trauner Angew. Chem., Int. Ed. 47 2008 8100 8103
43. M.E. Jung, and K.M. Halweg Tetrahedron Lett. 22 1981 3929 3932
44. D.A. Smith, K. Sakan, and K.N. Houk Tetrahedron Lett. 27 1986 4877 4880
45. S.C. Watson, and J.F. Eastham J. Organomet. Chem. 9 1967 165 167
46. R.A. Ellison, R. Griffin, and F.N. Kotsonis J. Organomet. Chem. 36 1972 209 213
47. P.C. Stanislawski, A.C. Willis, and M.G. Banwell Org. Lett. 8 2006 2143 2146
48. P.E. Tessier, N. Nguyen, M.D. Clay, and A.G. Fallis Org. Lett. 7 2005 767 770