Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 22, 1992 - Issue 13
30
Views
9
CrossRef citations to date
0
Altmetric
Original Articles

A New Efficient and Stereoselective Synthesis of 1,3E,5Z-Undecatriene

, , , &
Pages 1839-1844 | Accepted 20 Feb 1992, Published online: 23 Sep 2006

References

  • Chrétien-Bessière , Y. , Gamero , J. , Benezet , L. and Peyron , L. 1967 . Bull. Soc. Chim. Fr. , : 97
  • Naves , Y. R. 1967 . Bull. Soc. Chim. Fr. , : 97
  • Gaudin , J.-M. and Morel , C. 1990 . Tetrahedron Lett. , 31 : 5749 See and reference 3 cited therein which gives all known syntheses at this date
  • Fugier , C. , Leroux , M. , Normant , J. F. and Alexakis , A. Eur. Pat. Appl. EP 203,615 . 31 May 1985 . (ORIL S.A.) The present work was patented
  • Näf , F. , Decorzant , R. , Thommen , W. , Willhalm , B. and Ohloff , G. 1975 . Helv. Chim. Acta , 58 : 1016
  • In their work, Näf et al4, prepared the Z-dialkenyl cuprate from Z1-bromo-1-heptene (→ Li → “Cu”)
  • Normant , J. F. and Alexakis , A. 1981 . Synthesis , : 841
  • Jabri , N. , Alexakis , A. and Normant , J. F. 1981 . Tetrahedron Lett. , 22 : 959
  • Jabri , N. , Alexakis , A. and Normant , J. F. 1983 . Bull. Soc. Chim. Fr. II , : 321 and 332
  • Gardette , M. , Jabri , N. , Alexakis , A. and Normant , J. F. 1984 . Tetrahedron , 40 : 2741
  • Alexakis , A. and Duffault , J. M. 1988 . Tetrahedron Lett. , 29 : 6243
  • Näf , F. and Decorzant , R. 1974 . Helv. Chim. Acta , 57 : 1309
  • Norris , W. P. 1959 . J. Org. Chem. , 24 : 579
  • Johnson , J. R. 1942 . Org. React. , 1 : 210 experiment p. 252
  • Wenkert , E. , Michelotti , E. L. and Swindell , C. S. 1979 . J. Am. Chem. Soc. , 101 : 2246
  • Wenkert , E. , Ferrara , T. W. and Michelotti , E. L. 1979 . J. Chem. Soc, Chem. Comm. , : 637
  • Okamura , H. , Miura , M. and Takei , H. 1979 . Tetrahedron Lett. , 20 : 43
  • Wadman , S. , Whitby , R. , Yeates , C. , Kocienski , P. and Cooper , K. 1987 . J. Chem. Soc, Chem. Comm. , : 241
  • Everhardus , R. H. , Peterse , A. , Vermeer , P. , Brandsma , L. and Arens , J. F. 1974 . Rec. Trav. Chim. Pays-Bas , 93 : 90 Prepared according to using LDA/THF instead of LiNH2/NH3
  • Fiandese , V. 1990 . Pure and Appl. Chem. , 62 : 1987 This result should be compared with the good yields obtained by Naso and Fiandese in their Nickel catalyzed coupling of phenylthio dienes with alkyl Grignard reagents. See
  • Hopkins , P. B. and Fuchs , P. L. 1978 . J. Org. Chem. , 43 : 1208
  • Wenkert , E. , Michelotti , E. L. , Swindell , C. S. and Tingoli , M. 1984 . J. Org. Chem. , 49 : 4894
  • Murahashi , S.-I. , Yamamura , M. , Yanagisawa , K.-I. , Mita , N. and Kondo , K. 1979 . J. Org. Chem. , 44 : 2408 The corresponding bromides and iodides are, of course, even more reactive but more costly
  • Klebanskii , A. L. , Sorokina , R. M. and Khavin , Z. Ya. 1947 . J. Gen. Chem. , 17 : 235
  • 1948 . Chem. Abstr. , 42 : 514h
  • Keegstra , M. A. , Verkruijsse , H. D. , Andriga , H. and Brandsma , L. 1991 . Synth. Comm. , 21 : 721
  • Fauvarque , J. F. and Jutand , A. 1981 . J. Organomet. Chem. , 209 : 109
  • Jabri , N. , Alexakis , A. and Normant , J. F. 1983 . Bull. Soc. Chim. Fr. , : 321
  • Dreiding , A. S. and Pratt , R. J. 1954 . J. Am. Chem. Soc. , 76 : 1902
  • Harwell , K. E. and Hatch , L. F. 1955 . J. Am. Chem., Soc. , 77 : 1682
  • Whitesides , G. M. , Casey , C. P. and Krieger , J. K. 1971 . J. Am. Chem. Soc. , 93 : 1379

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.