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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 22, 1992 - Issue 14
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Original Articles

Further Studies on Quinone Diels-Alder Reactions with 1,3,3-Trimethyl-2-vinylcyclohexenes: Regioselective Synthesis of 12-Methyl-podocarpane Diterpenes and Isolation of a Hetero Diels-Alder Product from 1,4-Benzoquinone

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Pages 2031-2042 | Received 11 Mar 1992, Published online: 23 Sep 2006

References

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  • Dev , S. and Renuka , M. 1986 . CRC Handbook of Terpenoids-Diterpenoids , Vol. III , Boca Raton, FL : CRC Press .
  • Ishii , H. , Ohtake , R. , Okida , H. , Mitsui , H. and Ikeda , N. 1970 . J. Pharm. Soc. Jpn. , 90 : 1283 b) Kirkemo, C.L. and White, J.D. J. Org. Chem. 1985, 50, 1318
  • Diene 1b was prepared as the major fraction of a ∼2–3,1 mixture of 1b and its Z-isomer. The mixture was used as is and recovery and 1H NMR analysis of starting material indicated that the minor isomer did not react. 1
  • Bax , A. and Summers , M. F. 1986 . J. Am. Chem. Soc. , 108 : 2093
  • Barltrop , J. and Hesp , B. 1965 . J. Chem. Soc. , : 5182 Photochemical reactions of 1,4-benzoquinone with dienes are known to produce dihydrospiropyrans (4+2 cycloadducts involving the C=O group), presumably via a stepwise process, see a), b) Bruce, J.M. Quart. Rev., Chem. Soc., 1967, 21, 405. c) Wilson, R.M., Gardner, E.J., Elder, R.C., Squire, R.H. and Florian, L.R. J. Am. Chem. Soc., 1974, 96, 2955
  • Guay , V. and Brassard , P. 1984 . Tetrahedron , 40 : 5039 a), See also b) Simoneau, B. and Brassard, P. Tetrahedron, 1986, 42, 3767
  • Echavarren , A. M. and Stille , J. K. 1988 . J.Am. Chem. Soc. , 110 : 4051
  • Boisvert , L. and Brassard , P. 1988 . J. Org. Chem. , 53 : 4052
  • Finley , K. T. 1988 . The Chemistry of the Quinonoid Compounds , Edited by: Patai , S. and Rappoport , Z. Vol. 2 , 537 New York : Wiley-Interscience . For an extensive review, see, Part 1
  • For general experimental procedures, see reference 1

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