Study for Total Synthesis of Bruceantin Analogue(Ⅰ)

Bruceantin 유사체의 전합성에 대한 연구 (Ⅰ)

  • 주정호 (동국대학교 이과대학 화학과) ;
  • 최정진 (동국대학교 이과대학 화학과) ;
  • 김홍범 (동국대학교 이과대학 화학과)
  • Published : 19940100

Abstract

The synthetic pathway of ethyl $({\pm})$-8-oxo-10-oxa-l'H-spiro[1, 3]dioxolane-4,4'-tricyclo [9.2.1.0 1,6]dodec-6-ene-9-carboxylate (7), an important intermediate for the total synthesis of bruceantin analogue, was developed. Ethyl 2-cyclohexanonecarboxylate and methyl vinyl ketone were employed as starting materials. Robinson annulation, allylic oxidation, regiospecific acylation and the formation of epoxy methano bridge ring were studied. 4,4a,5,6,7,8-Hexahydro-4a-hydroxy-2(3H)naphthalenone (14) was synthesized utilizing the unusual decarboethoxylation reaction discovered during ketalization of octalone (3).

Keywords

References

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