• Title/Summary/Keyword: Annulation

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Synthesis of Tetracyclic 5-Azaindole Analogues by Palladium-Catalyzed Sequential Annulation

  • Sung, Nack-Do;Yang, Ok-Kyung;Kang, Song-Su;Yum, Eul-Kgun
    • Bulletin of the Korean Chemical Society
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    • v.25 no.9
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    • pp.1351-1354
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    • 2004

  • Tetracyclic 5-azaindole analogues were prepared by palladium-catalyzed sequential annulation of benzylidene(3-iodopyridinyl-4-yl)amine and 1-aryl substituted internal alkynes under $Pd(OAc)_2,\;n-Bu_4NCl,\;and Et_3N\;at\;120^{\circ}C.$ The synthetic procedure showed possible diversification of tetracyclic 5-azaindole analogues by varying the 1-aryl substituent in internal alkynes.

  • https://doi.org/10.5012/bkcs.2004.25.9.1351 인용 PDF KSCI

Study for Total Synthesis of Bruceantin Analogue(Ⅰ) (Bruceantin 유사체의 전합성에 대한 연구 (Ⅰ))

  • Ju, Jeong Ho;Choe, Jeong Jin;Kim, Hong Beom
    • Journal of the Korean Chemical Society
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    • v.38 no.1
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    • pp.80-86
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    • 1994

  • 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).

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