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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 5, 1975 - Issue 5
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Original Articles

An Approach to the Synthesis of Bakkenolide A

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Pages 353-358 | Received 22 Apr 1975, Published online: 06 Dec 2006

References

  • Chemical Research Department, Pfizer Ltd., Sandwich, Kent, England
  • Shirahata , K. , Kato , T. , Kitahara , Y. and Abe , N. 1969 . Tetrahedron , 25 : 4671 and references cited therein
  • Evans , D. A. and Sims , C. L. 1973 . Tetrahedron Lett. , : 4691
  • Rüchardt , C. , Eichler , S. and Panse , P. 1963 . Angew. Chem. Int. Ed. , 2 : 619
  • Characterised as the phenyl urethane derivative6
  • Compound has satisfactory elemental analysis and spectral data
  • Three reaction-isolation cycles were necessary for complete conversion to 3
  • Schöllkopf , U. and Paust , J. 1963 . Angew. Chem. , 75 : 670
  • Presumably as a mixture of exo- and endo-isomers
  • Reaction of 7 with dichloromethyl methyl ether presumably forms a chloroacetal which is converted into the corresponding iodoacetal by reaction with lithium iodide. Halogen metal exchange followed by alkylation with methyl iodide would then given 8
  • Wenkert , E. , Mueller , R. A. , Reardon , E. J. , Sathe , S. S. , Scharf , D. J. and Tosi , G. 1970 . J. Amer. Chem. Soc. , 92 : 7428
  • Sakan , F. , Hashimoto , H. , Ichihara , A. , Shirahama , H. and Matsumoto , T. 1971 . Tetrahedron Lett. , : 3703
  • Characterised as the semicarbazone derivative6
  • Marshall , J. A. , Pike , M. T. and Carroll , R. D. 1966 . J. Org. Chem. , 31 : 2933
  • Identical to a sample6 prepared by an alternate route (T. J. Brocksom and M. G. Constantino, unpublished results)
  • Methoden der Organishen Chemie (Houben-Weyl) Vol. Vl/2, 591 (1963)

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