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

A Total Synthesis of (±)-Trichodiene

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Pages 443-445 | Received 17 May 1976, Published online: 06 Dec 2006

References

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  • All new compounds reported herein gave satisfactory elemental analyses
  • The diastereomeric ratio was determined (glc) after hydrolysis of the tetrahydropyranyl protecting group (p-TsOH, CH3OH), oxidation of the alcohol (CrO3, H2SO4, H2O, acetone), and esterification of the resulting carboxylic acid (CH2N2, ether)
  • Birch , A. J. , MacDonald , P. L. and Powell , V. H. 1970 . J. Chem Soc., C , : 1419
  • 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. Bower, J. Org. Chem., 21, 1547 (1956)
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  • GLC analysis was performed on a 5-ft., stainless steel, 0.125 in. column packed with 3% SE-30 on Varaport 30, 100/120 mesh (Varian), flow rate 15 ml/min, 170° column temperature
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  • Dimethylsulfoxide was distilled three times from a 95:5 ratio of calcium hydride (−40 mesh): sodium amide at ∼15 mm on to freshly activated molecular sieves type 4A
  • We are grateful to Professor S. Nozoe for providing ir and nmr (100 MHz) spectra of natural trichodiene (1), trichoenone (9a), and trichodiene monoepoxide

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