Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

A New Chiral Synthetic Route to (+)-Isocarbacyclin

  • HoKoon Park (Organic Chemistry Laboratory I, Korea Institute of Science & Technology) ;
  • Yong Sup Lee (Organic Chemistry Laboratory I, Korea Institute of Science & Technology) ;
  • Shim Sang Chul (Deparment of Chemistry. Korea Advanced Institute of Science & Technology)
  • Published : 1993.02.20
Download PDF
⟨ Previous Next ⟩

Abstract

A synthetic route to (+)-isocarbacyclin starting from (-)-tricyclo[3.3.0.0$^{2.8}$]octan-3-one 6 is described. The key intermediate 4 has been synthesized from 6 by a sequential introduction of methoxycarbonyl group at C-12 and the oxygen functionality at C-9${\alpha}$(PG numbering) for the construction of ${\alpha}-and\;{\omega}$-side chain, and then converted to isocarbacyclin methyl ester 2.

Keywords

References

  1. Nature v.263 S. Moncada;R. Gryglewski;S. Bunting;J. R. Vane
  2. Prostaglandins v.13 G. J. Dusting;S. Moncada;J. R. Vane
  3. Tetrahedron Lett. v.24 M. Shibasaki;Y. Torisawa;S. Ikegami
  4. Chem. Pharm. Bull. v.37 M. Sodeoka;Y. Okawa;T. Mase;M. Shibasaki
  5. Tetrahedron Lett. v.28 S. Hashimoto;T. Shinoda;T. Honda;S. Ikegami
  6. Tetrahedron Lett. v.27 K. Bannai;T. Tanaka;A. Okamura;S. Sugiura;K. Manabe;K. Tomimori;S. Kurozumi
  7. Tetrahedron Lett. v.25 Y. Ogawa;M. Shibasaki
  8. J. Chem. Soc. Chem. Commun. Y. Torisawa;H. Okabe;S. Ikegami
  9. J. Am. Chem. Soc. v.106 M. Demuth;S. Chandrasekhar;K. Schaffner
  10. Angew. Chem. Int. Ed. Engl. v.21 M. Demuth;K. Schaffner
  11. Tetrahedron v.42 K. Mori;M. Tsuji
  12. J. Org. Chem. v.44 S. Iguchi;M. Hayashi;H. Yamamoto
  13. Synthesis M. Huckstep;J. K. Taylor

Cited by

  1. ChemInform Abstract: A New Chiral Synthetic Route to (+)-Isocarbacyclin. vol.24, pp.46, 1993, https://doi.org/10.1002/chin.199346251
  2. Novel synthetic strategies for the preparation of prostacyclin and prostaglandin analogues – off the beaten track vol.2007, pp.21, 1993, https://doi.org/10.1039/b617693n