Bulletin of the Korean Chemical Society

  • 제7권3호
  • /
  • Pages.166-169
  • /
  • 1986
  • /
  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
권호 표지
DOI QR코드

DOI QR Code

Synthesis of a Conformationally-rigid Etorphine Analogous

  • 발행 : 1986.06.20
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

In order to synthesize conformationally rigid etorphine analogues having potentially interesting pharmacological activities, synthesis of compound 3 by the reaction of compound 4 and compound 5 via intramolecular Diels-Alder reaction has been attempted. However, the reaction did not go well and the compound 3 would not be isolated. Therefore, intermolecular Diels-Alder reaction using dimethyl acetylene dicarboxylate was attempted. As shown in scheme 2, Diels-Alder adduct 9 was converted into the target molecule 14 containing the new [2.2.2] bicyclo octane ring in good yields.

키워드

참고문헌

  1. J. Med. Chem. v.17 B.T. Belleau;F.R. Ahmod;A.D. Hardy
  2. Proc. Natl. Acad. Sci. USA v.71 A.P. Feinberg;I. Greese;S.H. Sander
  3. J. Am. Chem. Soc. v.89 K.W. Bentley;M.E. Hardy
  4. J. Chem. Soc.(C) J.W. Lewis;M.J. Readhead;I.A. Selby;A.C.B. Smith;C.A. Young
  5. J. Med. Chem. v.23 L.S. Schwab
  6. J. Org. Chem. v.22 S.N. Reameritz;A.R. Dershowitz
  7. Angew. Chem. Int. Ed. Engl. v.18 D. Sternbach;M. Shibuya
  8. Biochem. Biophysic. Acta. v.144 W.J. Batlman;H.N.O. Schmid
  9. Tetrahedron Lett. E.J. Corey;J.W. Suggs
  10. J. Org. Chem. v.42 M.E. Jung;M.A. Lyser
  11. J. Org. Chem. v.44 G.A. Olah;S.C. Narang
  12. J. Chem. Soc. J.W. Lewis;W.I. Rushworth
  13. Tetrahedron Lett. T.R. Kelly
  14. Chem. Ber. v.89 M. Meerwein
  15. Biochem. Biophys. Acta. v.144 W.J. Baumann;H.N.O. Schmid
  16. Angew. Chem. Int. Ed. Engl. v.19 D. Sternbach;M.A. Shihya
  17. J. Am. Chem. Soc. v.89 K.W. Bentley;D.G. Hardy

피인용 문헌

  1. N-Demethylation of Alkaloids vol.1, pp.10, 1986, https://doi.org/10.1177/1934578x0600101008