The Synthesis of Shihunine via the Cyclopropyl Ketimine → Pyrroline Rearrangement

References

• Cloke , J. B. 1929 . J. Amer. Chem. Soc. , 51 : 1174
   Google Scholar
• Cloke , J. B. , Baer , L. H. , Robbins , J. M. and Smith , G. E. 1945 . J. Amer. Chem. Soc. , 67 : 2155
   Google Scholar
• Stevens , R. V. and Lai , J. T. 1972 . J. Org. Chem. , 37 : 2138 and references cited therein
   PubMed Web of Science ®Google Scholar
• Breuer , E. and Stein , Y. 1968 . Israel J. Chem. , 6 : 901
   Google Scholar
• Breuer , E. and Melumad , E. 1969 . Tetrahedron Letters , : 3595
   Google Scholar
• Breuer , E. and Melumad , D. 1972 . J. Org. Chem. , 37 : 3949
   Google Scholar
• Inubushi , Y. , Tsuda , Y. , Konita , T. and Matsumoto , S. 1968 . Chem. Pharm. Bull. (Tokyo) , 16 : 1014 Chem. Abstr., 69, 87256j (1968)
   Google Scholar
• Onaka , T. 1965 . Yakugaku Zasshi , 85 : 839 For synthesis of shihunine from dimethyl phthalate and 1-methyl-2-pyrrolidinone see: Chem. Abstr., 63, 18183f (1965)
   Google Scholar
• Keto acid II was prepared from the monochloride monomethyl ester of phthalic acid and dicyclopropyl cadmium. Details of this synthesis and of other reactions of II will be described elsewhere
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• Satisfactory elemental analysis and mass spectral data were obtained for this compound
   Google Scholar
• We wish to thank Prof. Y. Inubushi of Kyoto University for furnishing an authentic sample of shihunine picrate
   Google Scholar
• Deutsch , J. and Sklarz , B. 1972 . Israel J. Chem. , 10 : 51
   Google Scholar