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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 6, 1976 - Issue 7
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Original Articles

A Stereoselective and Regioselective Total Synthesis of (π)-Trichodiene

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Pages 485-488 | Received 23 Jun 1976, Published online: 01 Feb 2007

References

  • Nozoe , S. and Machida , Y. 1972 . Tetrahedron , 28 : 5105 Y. Machida and S. Nozoe, Tetrahedron Lett., 2671 (1970)
  • Machida , Y. and Nozoe , S. 1972 . Tetrahedron , 28 : 5113 Tetrahedron Lett., 1969 (1972)
  • Evans , R. and Hanson , J. R. 1976 . J. Chem. Soc. Perkin I , : 326
  • Welch , S. C. , Rao , A. S.C. P. and Wong , R. Y. 1976 . Synthetic Commun. , 6 Compound 3 was prepared by a highly stereoselective alkylation sequence
  • Bowden , K. , Heilbron , I. M. , Jones , E. R. H. and Weedon , B. C. L. 1946 . J. Chem. Soc. , : 39 C. Djerassi, R. R. Engle, and A. Bowers, J. Org. Chem., 21, 1547 (1956)
  • Compound 4 was initially isolated as a 96:4 ratio of diastereomers. The opposite alkylation sequence first using 5-bromo-1-pentene, second using methyl iodide followed by oxidative cleavage (OsO4, NaIO4, H2O t-BuOH), Jones' reagent, and esterification (CH2N2, Et2O) gives a diastereomeric mixture with a ratio of 2:98 where compound 4 is the minor isomer (see reference 4)
  • All new compounds reported herein gave satisfactory elemental and/or high resolution mass spectral analyses
  • Thyagarajan , B. S. 1954 . Chem. Reviews , 54 : 1029 D. E. Wolf and K. Folkers, Org. Reactions, 6, 449 (1951); C. R. Hauser and B. E. Hudson, Org. Reactions, 1, 274 (1942)
  • Kruger , C. , Rochow , E. G. and Wannagat , U. 1963 . Chem. Ber. , 96 : 2131
  • Parish , E. J. and Miles , D. E. 1973 . J. Org. Chem. , 38 : 1223
  • Jensen , N. P. and Johnson , W. S. 1967 . J. Org. Chem. , 32 : 2045
  • Gupta , A. S. and Dev , S. 1963 . J. Chromatog. , 12 : 189
  • Maercker , A. 1965 . Org. Reactions , 14 : 270
  • We are grateful to Professor S. Nozoe for providing ir and nmr (100 MHz) spectra of trichoenone (10a), trichodiene (1), and trichodiene monoepoxide

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