Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 22, 1992 - Issue 7
47
Views
16
CrossRef citations to date
0
Altmetric
Original Articles

Conformationally Constrained Amino Acids.1 on the Synthesis of 4-Substituted 8-Membered Cyclic Tryptophan Derivatives

, &
Pages 1039-1048 | Received 24 Oct 1991, Published online: 24 Sep 2006

References

  • Chung , J. Y. L. , Wasicak , J. T. , Arnold , W. A. , May , C. S. , Nadzan , A. M. and Holladay , M. W. 1990 . J. Org. Chem. , 55 : 270 – 275 . Part 2 in the series “Conformational Constrained Amino Acids”. For part 1, “On the Synthesis and Optical Resolution of 3-Substituted Proline Derivatives”, see:
  • Momany , F. A. and Chuman , H. 1986 . Methods Enzymol. , 124 : 3
  • Marshall , G. R. 1982 . Chemical Recognition in Biological Systems , Edited by: Creighton , A. M. and Turner , S. 279 London : The Chemical Society .
  • Arison , B. H. , Hirschmann , R. and Veber , D. F. 1978 . Bioorganic Chem. , 7 : 447
  • Nadzan , A. M. , Garvey , D. S. , Holladay , M. W. , Shiosaki , K. , Tufano , M. D. , Chung , J. Y. L. , May , P. D. , May , C. S. , Lin , C. W. , Miller , T. R. , Witte , D. G. , Bianchi , B. R. , Wolfram , A. W. , Burt , S. and Hutchins , C. W. 1992 . Peptides, Chemistry and Biology , Edited by: Smith , J. and Rivier , J. Leiden : ESCOM . in press
  • Mascal , M. and Moody , C. J. 1988 . J. Chem. Soc. Chem. Commun. , : 587
  • Yonemitsu , O. , Cerutti , P. and Witkop , B. 1966 . J. Amer. Chem. Soc. , 88 : 3941
  • Gilchrist , T. L. , Lingham , D. A. and Roberts , T. G. 1989 . J. Chem. Soc. Chem. Commun. , : 1089
  • Gilchrist , T. L. and Roberts , T. G. 1983 . J. Chem. Soc. Perkin Trans. I , : 1283
  • Ottenheijm , H. C. J. , Plate , R. , Noordik , J. H. and Herscheid , D. M. 1982 . J. Org. Chem. , 47 : 2147
  • Matsumoto , M. and Watanabe , N. 1984 . Heterocycles , 22 : 2313
  • Matsumoto , M. , Watanabe , N. and Ishida , Y. 1986 . Ibid , 24 : 2611
  • Ponticello , G. S. and Baldwin , J. J. 1979 . J. Org. Chem. , 44 : 4003
  • Drinkwater , D. J. and Smith , P. W. G. 1971 . J. Chem. Soc. (C) , : 1305
  • Jager , V. , Grund , H. and Schwab , W. 1979 . Angew. Chem. Internat. Edn. , 18 : 78
  • Energy calculations for cyclization of 5 to 6 via the tetrahedral intermediate revealed 6 is 75 Kcal/mol higher in energy than 5 with an activation energy of DG∗=12.2 kcal/mol at 298°K and 79 Kcal/mol higher in energy with an activation energy of DG∗=13.2 Kcal/mol at 410°K

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.