Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 13-14
62
Views
23
CrossRef citations to date
0
Altmetric
Original Articles

Stereospecific Synthesis of S,S-Statine and its Congeners

, &
Pages 2573-2583 | Received 07 Apr 1989, Published online: 24 Oct 2006

References

  • Boger , J. , Lohr , N. S. , Ulm , E. H. , Poe , K. , Blaine , E. H. , Fanelli , G. M. , Lin , T. Y. , Payne , L. S. , Schorn , T. W. , LaMont , B. I. , Vassil , T. C. , Stabilito , I. I. , Veber , D. F. , Rich , D. H. and Bopari , A. S. 1983 . Nature , 303 : 81
  • Boger , J. , Payne , L. S. , Perlow , D. S. , Lohr , N. S. , Pow , H. , Blaine , E. H. , Ulm , E. H. , Schorn , T. W. , LaMont , B. L. , Lin , T. Y. , Kamai , M. , Rich , D. H. and Veber , D. F. 1985 . J. Med. Chem. , 28 : 1779
  • Kokubu , T. and Hiwada . 1987 . Drugs of Today , 23 ( 2 ) : 101
  • Smith , S. G. , Seymour , A. A. , Mazack , E. K. , Boger , J. and Blaine , E. H. 1987 . Hypertension , 9 ( 2 ) : 150
  • Rich , D. H. , Sun , E. T. and Boparai , A. S. J. 1978 . J. Org. Chem. , 43 : 3624
  • Liu , W. S. , Smith , S. C. and Glover , G. I. 1979 . J. Med. Chem. , 22 : 577
  • Hayon , A. F. , Fehrentz , J. A. , Chapleur , Y. and Castro , B. 1983 . Bull. Soc. Chim Fr. , : 207
  • Woo , P. W. K. 1985 . Tetrahedron Lett. , 25 : 2973
  • Repine , J. U. S. Pat. . 4,650,897 . 1987 .
  • Kogen , H. and Nishi , T. 1987 . J. Chem. Soc., Chem. Commun. , : 311
  • Andrew , R. G. , Conrow , R. E. , Elliott , J. D. , Johnson , W. S. and Ramezani , S. 1987 . Tetrahedron Lett. , 28 ( 52 ) : 6535
  • Savrda , J. and Descoins , C. 1987,1901 . Synthetic Communications , 17 ( 16 )
  • Devant , R. H. and Radunz , H. E. 1988 . Tetrahedron Lett. , 29 ( 19 ) : 2307
  • Morishima , H. , Sawa , T. , Takita , T. , Aoyagi , T. , Takeuchi , T. and Umezawa , H. 1974 . J. Antibiot. , 27 : 267
  • Steulmann , R. and Klostermeyer , H. 1975 . Liebigs Ann. Chem. , : 2245
  • Rich , D. H. , Sun , E. T. and Ulm , E. 1980 . J. Med. Chem. , 23 ( 1 ) : 27
  • Dufour , M. N. , Jouin , P. , Poncet , J. , Pantaloni , A. and Castro , B. 1986 . J. Chem. Soc., Perkin Trans. I , : 1895
  • Harris , B. D. , Bhat , K. L. and Joullie , M. M. 1987 . Tetrahedron Lett. , 28 ( 25 ) : 2837
  • Raddatz , P. , Radunz , H. E. , Schneider , G. and Schwartz , H. 1988 . Angew. Ehem. Tnt. Ed. Engl. , 3 : 426
  • Schuda , P. F. , Greenlee , W. J. , Chakravarty , P. K. and Eskola , P. 1988 . J. Org. Chem. , 53 : 873
  • Maibaum , J. and Rich , D. H. 1988 . J. Org. Chem. , 53 : 869
  • Nishi , T. , Kitamura , H. , Ohkuma , T. and Noyori , R. 1988 . Tetrahedron Lett. , 29 ( 48 ) : 6327
  • Kinoshita , H. , Aburaki , S. , Hagiwara , A. and Imai , J. 1973 . J. Antibiot. , 26 : 249
  • Danishefsky , S. , Kobayashi , S. and Kerwin , J. F. Jr. 1982 . J. Org. Chem. , 47 : 1981
  • Sakaitani , H. and Ohfune , Y. 1987 . Tetrahedron Lett. , 28 ( 34 ) : 3987
  • Mulzer , J. , Buttelmann , B. and Hunch , W. 1988 . Liebigs Ann. Chem. , : 445
  • Katsuki , T. and Yamaguchi , M. 1976 . Bull. Chem. Soc. Japan , 49 : 3287
  • Jouin , P. and Castro , B. 1987 . J. Chem. Soc. Perkin Trans. I , : 1177
  • Mulholland , T. P. C. , Foster , R. and Haydock , J. 1972 . Chem. Soc. Perkin Trans. , 1 : 2121 Stork, G. and Szajewski, P., J. Amer. Chem. Soc, 1974, 96, 5787; Jones, R. C. F. and Sumaria. Tetrahedron Lett., 1974, No. 34, 3173; Vedejs, E., Campbell, Jr., J. B., Gadwood, R. C., Rodgers, J. D., Spear, K. L. and Watanabe, Y., J. Org. Chem. 1982, 47, 1534.
  • Morisawa , Y. , Yabe , Y. , Kataoaka , M. , Iijima , Y. , Kokubu , T. and Hiwada , K. European European Pat. EP . 186,977 . 1985 .
  • Hiwada , K. , Kokubu , T. , Murakami , E. , Muneta , S. , Morisawa , Y. , Yabe , Y. , Koike , H. and Iijima , Y. 1988 . Hypertension , 11 : 708
  • Flynn , D. L. , Zelle , R. E. and Grico , P. A. 1983 . J. Org. Chem. , 48 : 2424
  • This material was used as such in the next step. In one run purification by silica gel chromatography, eluting with 2:1 hexane-ethyl acetate, to remove traces of impurities, resulted in better quality products in subsequent steps.
  • The use of freshly prepared sodium ethoxide improved the quality of reaction product.

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.