Corrigendum to "A three carbon (n+1+2) ring expansion method for the synthesis of macrocyclic enones. Application to muscone synthesis" [Tetrahedron 64(23) (2008) 5497-5501] (DOI:10.1016/j.tet.2008.03.109);A three-carbon (n+1+2) ring expansion method for the synthesis of macrocyclic enones. Application to muscone synthesis

Tetrahedron

Volumn 64, Issue 23, 2008, Pages 5497-5501

  Erden, Ihsan ^a   Cao, Weiguo ^a   Price, Mary ^a   Colton, Michael ^a  

^a SAN FRANCISCO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANONE; ALLENE DERIVATIVE; BICYCLO COMPOUND; CARBENOID; CARBON; CYCLOALKENE; DIAZABICYCLOUNDECANE; DIBROMOCARBENE; DICHLOROKETENE; KETENE DERIVATIVE; LITHIUM DERIVATIVE; MACROCYCLIC COMPOUND; MACROCYCLIC ENONE; METHANOL; METHYLLITHIUM; MUSCONE; SILANE DERIVATIVE; TRIMETHYLSILYL IODIDE; ZINC;

ADDITION REACTION; ARTICLE; CATALYSIS; DECHLORINATION; HYDROGENATION; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 43049123369     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.05.099     Document Type: Erratum

References (60)

1. (a) A.J. Weinheimer C.W.J. Chang J.A. Matson Fortschr. Chem. Org. Naturst. 36 1979 285
2. (b) J.R. Hanson Nat. Prod. Rep. 1 1984 171
3. (c) Macrolide Antibiotics ; Omura, S., Ed.; Academic: New York, NY, 1984;
4. (d) F. Sorm Fortschr. Chem. Org. Naturst. 19 1961 1
5. B.D. Mookherjee R.A. Wilson E.T. Theimer Fragrance Chemistry 1982 Academic New York, NY 433
6. For recent syntheses, see:
7. (a) G. Ruedi H.-J. Hansen Tetrahedron Lett. 45 2004 5143
8. (b) Y. Hisanaga Y. Asumi M. Takahashi Y. Shimizu N. Mase H. Yoda K. Takabe Tetrahedron Lett. 49 2008 548
9. (c) P. Scafato A. Larocca C. Rosini Tetrahedron: Asymmetry 17 2006 2511
10. (a) I. Erden E.M. Sorensen Tetrahedron Lett. 23 1983 2731
11. (b) A.I. Erden A. de Meijere Tetrahedron Lett. 24 1983 3811
12. (c) I. Erden Tetrahedron Lett. 25 1984 1535
13. (d) I. Erden Tetrahedron Lett. 26 1985 5635
14. A three-carbon ring expansion methodology via cyclopentenone annulation to cyclododeacanone has been applied to muscone synthesis: J. Tsuji T. Yamada I. Shimizu J. Org. Chem. 45 1980 5209
15. See: The Merck Index, 13th Edition; for a review, see: G. Ohloff Fortschr. Chem. Forsch. 12 1969 185
16. Other ring expansion methodology based on dichloroketene cycloadditions have been reported:
17. (a) one-carbon ring expansion: A.G. Greene J.-P. Depres J. Am. Chem. Soc. 101 1979 4003
18. A.E. Greene M.-J. Luche A.A. Serra J. Org. Chem. 50 1985 3957
19. (b) two-carbon expansion: J.-P. Depres B. Navarro A.E. Greene Tetrahedron 45 1989 2989
20. (c) free-radical five- and six-carbon ring expansions: W. Zhang M.R. Collins K. Mahmood P. Dowd Tetrahedron Lett. 36 1995 2729 and references cited therein
21. (a) W.E. von Doering P.M. La Flamme Tetrahedron 2 1958 75
22. (b) W.R. Moore H.R. Ward J. Org. Chem. 27 1962 4179
23. (c) L. Skattebol Acta Chem. Scand. 17 1963 1683
24. (d) C.D. Gutsche D. Redmore Carbocyclic Ring Expansion Reactions 1968 Academic New York, NY
25. G.R. Krow Tetrahedron 43 1987 3 and references cited therein
26. (a) T.T. Tidwell Ketenes 1995 Wiley-Interscience New York, NY
27. (b) E. Lee-Ruff B. Halton Advances in Strain in Organic Chemistry Vol. I 1991 JAI London 167 213
28. (c) J.C. Namylso D.E. Kaufmann Chem. Rev. 103 2003 1485
29. (d) T.T. Tidwell Eur. J. Org. Chem. 2006 563
30. D.A. Bak W.T. Brady J. Org. Chem. 44 1979 107
31. L.R. Krepski A. Hassner J. Org. Chem. 43 1978 2879
32. G. Mehta H.S.P. Rao Synth. Commun. 15 1985 991
33. A.R. Pinder Synthesis 1980 425 and references cited therein
34. (a) P.W. Jeffs G. Molina M.W. Cass N.A. Cortese J. Org. Chem. 47 1982 3871
35. (b) G. Rosini R. Ballini Tetrahedron 39 1983 1085
36. B. Braillon J. Salaun J. Gore J.M. Conia Bull. Soc. Chim. Fr. 1964 1981
37. (a) M. Bertrand J.-L. Gras J. Gore Tetrahedron Lett. 1972 1189
38. (b) M. Bertrand R. Maurin J.-L. Gras G. Gil Tetrahedron 31 1975 849
39. (c) M. Bertrand J.-L. Gras J. Gore Tetrahedron 31 1975 857
40. I. Marko B. Ronsmans A.-M. Hesbain-Frisque S. Dumas L. Ghosez J. Am. Chem. Soc. 107 1985 2192
41. R.D. Miller D.R. McKean Tetrahedron Lett. 1980 2639
42. B.D. Mookherjee R.R. Patel W.O. Ledig J. Org. Chem. 36 1971 4124
43. Compound 12 has previously been prepared by Brady et al. by dichloroketene addition, generated from dichloroacetyl chloride with triethylamine, to 1,2-cyclononadiene: W.T. Brady J.D. Stockton A.D. Patel J. Org. Chem. 39 1974 236
44. J.M. Conia M.J. Robson Angew. Chem., Int. Ed. Engl. 14 1975 473 and references cited therein
45. K.E. Harding J.W. Trotter L.M. May J. Org. Chem. 42 1977 2715
46. J.R. Cagnon J. Marchand-Brynaert L. Ghosez J. Braz. Chem. Soc. 7 1996 371
47. (a) Z. Paryzek Blaszczyk Liebigs Ann. 1993 615
48. (b) Z. Paryzek Blaszczyk Liebigs Ann. 1995 341
49. A. Hassner S. Naidorf-Meir A.A. Frimer J. Org. Chem. 61 1996 4051
50. K.H. Chun T. Yoon Y.E.N. Shin C. Jo Y.-J. Jo H. Yun J. Oh Bull. Korean Chem. Soc. 26 2005 1104
51. N.A. Donskaya A.G. Bessmertnykh V.A. Drobysh Y.S. Shabarov Zh. Org. Khim. 23 1987 751
52. (a) J. Brown D.M. Pawar E.A. Noe J. Org. Chem. 68 2003 3420
53. (b) H. Nozaki T. Aratani T. Toraya R. Noyori Tetrahedron 27 1971 905
54. (c) K. Shea J.-S. Kim J. Am. Chem. Soc. 114 1992 3044
55. M. Makosza Pure Appl. Chem. 43 1975 439
56. A. Abad C. Agullo M. Arno E. Seoane Tetrahedron 42 1986 2429
57. E. Friedrich W. Lutz Chem. Ber. 113 1980 1245
58. (a) G. Ruedi H.-J. Hansen Helv. Chim. Acta 87 2004 1628
59. (b) G. Ruedi M.A. Oberli M. Nagel H.-J. Hansen Org. Lett. 6 2004 3179
60. J. Tsuji T. Yamada I. Shimizu J. Org. Chem. 45 1980 5211