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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 2, 1972 - Issue 1
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Original Articles

Total Synthesis of Dihydrocinchonamine

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Pages 55-61 | Received 05 Jan 1972, Published online: 03 Jan 2007

References

  • Taylor , W. I. 1965 . The Alkaloids Vol. VIII , 237 and vol. IX, page 73, 1968, R. H. P. Manske, Ed., Acaddcmic Press, N.Y.
  • Bohrmann , H. , Lau-Cam , C. , Tashiro , J. and Youngken , H. W. Jr. 1969 . Phytochemistry , 8 : 645
  • Arnaud , M. 1881 . Compt. Rand. Acad. Sci. , 93 : 593
  • Goutarel , R. , Janot , M.-M. , Prelog , V. and Taylor , W. I. 1950 . Helv. Chim. Acta , 33 : 150 W. I. Taylor, ibid, 33, 164 (1950)
  • Sawa , Y. K. and Matsumura , H. 1970 . Tetrahedron , 26 : 2923
  • Evstigreeva , R. P. , Chang-pai , C. and Precbazhenskii , N. A. 1960 . J. Gen. Chem. USSR , 30 : 495
  • Ochiai , E. , Kataoka , H. , Dodo , T. and Takahashi , M. 1962 . Chem. Pharm. Bull , 10 : 76 and earlier references cited therein
  • Ochiai , E. , IshiKawa , M. and Oka , Y. 1962 . Ann. Rept. ITSUU Lab , 12 : 29
  • Ishikawa , M. 1958 . Chem. Pharm. Bull , 6 : 71
  • Grathe , G. , Mitt , T. , Lee , H. L. and Uskoković , M. 1971 . J. Amer. Chem. Soc. , 93 : 5904
  • Yang , K. W. , Cannon , J. G. and Rose , J. G. 1970 . Tetrahedron Letters , : 1791
  • The numbering follows that for 2,2′-indolquinuclidine alkaloids
  • Sundberg , R. J. 1970 . The Chemistry of Indoles , Edited by: Bloomquist , A. T. 189 N.Y. : Academic Press .
  • Simultaneously and independently the Madelung indole synthsis of similar systems was thoroughly investigated by R. L. Augustine and his group (personal communication).
  • Silica gel Merck F-254 was treated with 0.1N sodium hydroxide activated at 140° for 20 min.
  • Oddo , B. and Cambieri , P. 1939 . Gazz. Chim. Ital. , 69 : 19
  • We thank Professor R. L. Augustine for supplying us with a small sample of dihydrocinchonamine.

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