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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 6, 1976 - Issue 1
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Original Articles

Synthesis of Prostanoids. I. A Highly Convergent Approach to 13-oxi-Prostanoids

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Pages 39-45 | Received 24 Sep 1975, Published online: 05 Dec 2006

References

  • May 1974 . May , Taken in part from the thesis presented by J. A. Noguez to Division de Estudios Superiores de 1a Facultad de Quimica, UNAM, in partial fulfillment for his Ph. D. degree. A portion of this work was presented in the IX Mexican Congress of Pure and Applied Chemistry, Zacatecas, México (May, 1974). See Rev. Soc. Quím. Méx. 18, 130 (1974), abstract 52
  • Spraggins , R. L. 1972 . Tetrahedron Lett. , : 4343
  • Greene , A. E. , Girard , G. R. and Kerwin , J. F. 1975 . Tetrahedron Lett. , : 937
  • Stork , G. 1968 . Pure and Appl. Chem. , 17 : 383 G. Stork, R. A. Kretchmer and R. H. Schlessinger, J. Amer. Chem. Soc. 90, 1647 (1968). For an extensive review of the literature on this subject see references cited under 5. See also: G. Stork, G. L. Nelson, F. Rouessac and O. Gringore, J. Amer. Chem. Soc. 93, 3091 (1971); R. A. Kretchmer, E. D. Mihelich and J. J. Waldron, J. Org. Chem. 26, 4483 (1972); J. L. Herrmann, M. H. Berger and R. H. Schlessinger, J. Amer. Chem. Soc. 95, 7923 (1973); G. Stork and M. E. Jung, J. Amer. Chem. Soc. 96, 3682 (1974); D. Seebach and R. Burstinghaus, Angew. Chem. Internat. Ed. Engl. 14, 57 (1975)
  • Posner , G. H. , Whitten , C. E. , Sterling , J. J. and Brunelle , D. J. 1974 . Tetrahedron Lett. , : 2591 G. H. Posner, J. J. Sterling, C. E. Whitten, C. M. Lentz and D. J. Brunelle, J. Amer, Chem. Soc. 97, 107 (1975)
  • Patterson , J. W. Jr. and Fried , J. H. 1974 . J. Org. Chem. , 39 : 2506 In this case, the enolate trapping reaction could not be made directly
  • Seebach , D. 1969 . Angew. Chem. Internat. Ed. Engl. , 8 : 639 For reviews see : and D. Seebach and M. Kolb, Chem. and Ind., 687 (1974). For recent acyl carbanions equivalents see : J. E. Baldwin, G. A. Hofle and O. W. Lever Jr., J. Amer. Chem. Soc., 96, 7125 (1974) (a thorough review of the recent literature is included there); R. K. Boeckman Jr. and K. J. Bruza, Tetrahedron Lett., 3365 (1974); T. Wakamatsu, K. Akasaka and Y. Ban, Tetrahedron Lett., 3879 (1974)
  • Corey , E. J. and Hegedus , L. S. 1969 . J. Amer. Chem. Soc. , 91 : 4926 Acyl carbonyl nickelate reagents
  • Mukaiyama , T. , Narasaka , K. and Furusato , M. 1972 . J. Amer. Chem. Soc. , 94 : 8641 Copper phenyl thioacetals
  • McMurry , J. E. and Melton , J. 1973 . J. Org. Chem. , 38 : 4367 Nitroalkanes
  • Stork , G. and Maldonado , L. A. 1974 . J. Amer. Chem. Soc. , 96 : 5272 “Protected” cyanohydrins
  • Herrmann , J. L. , Richman , J. E. and Schlessinger , R. H. 1973 . Tetrahedron Lett. , : 3271 Thioacetal monosulphoxides
  • Stork , G. and Maldonado , L. A. 1971 . J. Amer. Chem. Soc. , 93 : 5286 L. A. Maldonado, Rev. Soc. Quim. Méx., 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 : K. Deuchert, U. Hertenstein and S. Hunig, Synthesis, 777 (1973); S. Hunig and G. Wehner, Synthesis, 180, 391 (1975)
  • Ficini , J. , d'Angelo , J. and Noiré , J. 1974 . J. Amer. Chem. Soc. , 96 : 1213 For use of Stork “protected” cyanohydrin reagents in the synthesis of natural products see : J. A. Noguez, F. L. Malanco and L. A. Maldonado, Rev. Soc. Quim. Méx., submitted for publication; A. Casares and L. A. Maldonado, Synthetic Comm., submitted for publication
  • Hoaglin , R. I. and Hirsch , D. H. 1949 . J. Amer. Chem. Soc. , 71 : 3468
  • Corey , E. J. and Sachdev , H. S. 1973 . J. Amer. Chem. Soc. , 95 : 8483 For similar synthesis of 4 see : J. Martell and E. Toromanoff, Chem. Abst., 76, 24712d (1972)
  • Noack , K. and Jones , R. N. 1961 . Can. J. of Chem. , 39 : 2225
  • In addition to 6a and 7a, a 9% yield of a compound to which structure 8 is proposed was obtained
  • Bagli , J. F. and Bogri , T. 1972 . Tetrahedron Lett. , : 3815
  • We thank Professors G. Stork and P. Crabbéfor encouragement and advice throughout this work and Ing. Quím. F. Jauregui (Central Laboratory of Hacienda, México) for mass spectra determinations and his help in their interpretation
  • This work was partially supported by a grant from Cámara Nacional de la Industria de Productos Quimico‐Farmacéuticos

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