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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 6, 1976 - Issue 7
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Original Articles

Synthesis of Terpenoids. III. Total Syntheses of α-Bisabololone and α-Trans-Atlantone

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Pages 515-519 | Received 21 Jul 1976, Published online: 01 Feb 2007

References

  • March 1975 . March , Taken in part from the thesis presented by F. L. Malanco to Division de Estudios Superiores de la Facultad de Química, UNAM, in partial fulfillment for his Ph. D. degree
  • Stork , G. and Maldonado , L. A. 1971 . J. Amer. Chem. Soc. , 93 : 5286 96, 5272 (1974); L. A. Maldonado, Rev. Soc. Quim. Mex., 16, 200 (1972); G. Stork, J-C. Depezay and J. d'Angelo, Tetrahedron Lett., 389 (1975). For related work with α-trimethyl siloxy nitriles see: S. Hunig and G. Wehner, Synthesis, 391 (1975) and references cited therein
  • Casares , A. and Maldonado , L. A. 1976 . Synthetic Comm. , 6 : 11 J. A. Noguez and L. A. Maldonado, Synthetic Comm., 6, 39 (1976)
  • Bohlmann , F. and Rao , N. 1972 . Tetrahedron Lett. , : 1295
  • Gopichand , Y. and Chakravarti , K. K. 1974 . Tetrahedron Lett. , : 3851 In the course of this work the first total synthesis of this sesquiterpene was reported:
  • Manjarrez , A. , Ríos , T. and Guzmán , A. 1964 . Tetrahedron , 20 : 333 E. F. Lutz and G. M. Bailey, J. Amer. Chem. Soc., 86, 3899 (1964)
  • Corey , E. J. and Chaykovsky , M. 1962 . J. Amer. Chem. Soc. , 84 : 867 87, 1353 (1965)
  • Trost , B. M. and Salzmann , T. N. 1973 . J. Amer. Chem. Soc. , 95 : 6840
  • Farges , G. and Kergomard , A. 1969 . Bull. Soc. Chim. France , : 4476
  • Seebach , D. , Jones , N. R. and Corey , E. J. 1968 . J. Org. Chem. , 33 : 300 D. Seebach and E. J. Corey, J. Org. Chem., 40, 231 (1975)
  • Julia , M. , Julia , S. and Lanq-lois , H. 1965 . Bull. Soc. Chim. France , : 1007 The “protected” cyanohydrin 3 (bp 70°/0.2 mm.) was prepared from 3-methyl-crotonaldehyde, by conversion to the cyanohydrin (NaCN, AcOH-H2O-THF, O°) followed by protection with ethyl vinyl ether and a trace of TsOH (90–100% overall yield from the aldehyde
  • This reaction is now under extensive study by Dr. G. A. Garcia of this laboratories and his results are soon to be reported elsewhere
  • Crawford , R. J. , Eman , W. F. and Broaddus , C. D. 1972 . J. Amer. Chem. Soc. , 94 : 4298 For previous syntheses of this sesquiterpene see:, J. H. Babler, D. O. Olsen and W. H. Arnold, J. Org. Chem., 39, 1656 (1974); D. R. Adams, S. P. Bhatnagar, R. C. Cook-son and R. M. Tuddenham, Tetrahedron Lett., 3197 (1974)
  • Pande , B. S. , Krishnappa , S. , Bisarya , S. C. and Dev , S. 1971 . Tetrahedron , 27 : 841
  • We thank Camara Nacional de la Industria de Productos Químico-Farmacéuticos for partial support of our work

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