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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 25, 1995 - Issue 3
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Original Articles

A Convenient Synthesis of C-8 Oxo-eudesmane. Total Synthesis of (±)-Eudesma-5,7(11)-dien-8-one

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Pages 405-412 | Received 21 Jun 1994, Published online: 23 Sep 2006

References

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  • Kondo , K. and Hikino , H. 1979 . Bull. Chem. Soc. Jp. , 52 : 2439
  • Endo , J. , Nagasawara , M. and Yakugaku , Zasshi . 1974 . 94 : 1574 For the enantiomer of 3
  • Kondo , K. , Toyota , M. and Asakawa , Y. 1990 . Phytochemistry , 29 : 2197 see:
  • Coll , J. C. , Bowden , B. F. , Topiolas , D. M. , Willis , R. H. , Djura , P. , Streamer , M. and Trott , L. 1985 . Tetrahedron , 41 : 1085
  • Goldsmith , D. J. and Sakano , I. 1976 . J. Org. Chem. , 41 : 2095
  • Banerjee , A. K. , Gonzalez , N. C. and de Sepulveda , M. C. 1992 . J. Chem. Res.(S) , : 310 For a formal synthesis see
  • Heathcok , C. H. , Graham , S. L. , Pirrung , M. C. , Plavac , F. and White , C. T. 1983 . The Total Synthesis of Natural Products , Edited by: ApSimon , J. Vol.V , New York : John Wiley & Sons . Review for the synthesis of eudesmane skeleton see
  • Tsankova , T. , Ognyanov , I. and Norin , T. 1980 . Tetrahedron , 36 : 669
  • Still , W. and van Middlesworth , L. 1977 . J. Org. Chem. , 42 : 1258
  • Revial , G. and Pfau , M. 1991 . Organic Synthesis , 70 : 35 For the optically active octalone 7 see
  • Dunlap , N. K. , Sabol , M. R and Watt , D. S. 1984 . Tetrahedron Lett. , 25 : 5839
  • Caine , D. , Boucugnani , A. A. , Chao , S. T. , Dawson , J. B. and Ingwalson , P. F. 1976 . J. Org. Chem. , 41 : 1539
  • Corey , E. J. , Ohno , M. , Mitra , R. B. and Vatakencherry , P. A. 1964 . J. Am. Chem. Soc. , 86 : 478
  • Guerreiro , A. , Dematte , B. , D'Ambrosio , M. and Pietra , F. 1986 . J. Nat. Prod. , 49 : 608
  • In a reference 4, the authors also reduced the enone 4 with LAH to get a inseparable epimeric alcohols at C-8
  • Fagerlund , U. H. and Idler , D. R. 1957 . J. Am. Chem. Soc. , 79 : 6473

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