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Volumn 73, Issue 23, 2008, Pages 9320-9325

Construction of the adamantane core of plukenetione-type polycyclic polyprenylated acylphloroglucinols

Author keywords

[No Author keywords available]

Indexed keywords

ADAMANTANE; CHEMICAL EQUATIONS; FUNCTIONALIZED; MICHAEL REACTIONS;

EID: 57449085931     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801595y     Document Type: Article
Times cited : (29)

References (97)
  • 14
    • 0026574826 scopus 로고    scopus 로고
    • For bioactivity of PPAPs in general, see, for example: (a) Gustafson, K. R.; Blunt, J. W.; Munro, M. H. G.; Fuller, R. W.; McKee, T. C.; Cardellina, J. H.; McMahon, J. B.; Cragg, G. M.; Boyd, M. R. Tetrahedron 1992, 46, 10093-10102.
    • For bioactivity of PPAPs in general, see, for example: (a) Gustafson, K. R.; Blunt, J. W.; Munro, M. H. G.; Fuller, R. W.; McKee, T. C.; Cardellina, J. H.; McMahon, J. B.; Cragg, G. M.; Boyd, M. R. Tetrahedron 1992, 46, 10093-10102.
  • 25
    • 0037071205 scopus 로고    scopus 로고
    • For some recent synthetic studies toward the bicyclo[3.3.1]nonanone core of bicyclic PPAPs, see: (a) Usuda, H.; Kanai, M.; Shibasaski, M. Tetrahedron Lett. 2002, 43, 3621-3624.
    • For some recent synthetic studies toward the bicyclo[3.3.1]nonanone core of bicyclic PPAPs, see: (a) Usuda, H.; Kanai, M.; Shibasaski, M. Tetrahedron Lett. 2002, 43, 3621-3624.
  • 43
    • 26844495771 scopus 로고    scopus 로고
    • Total synthesis of PPAPs with a bicyclic core: (a) Kuramochi, A.; Usuda, H.; Yamatsugu, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 14200-14201.
    • Total synthesis of PPAPs with a bicyclic core: (a) Kuramochi, A.; Usuda, H.; Yamatsugu, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 14200-14201.
  • 74
    • 84925564613 scopus 로고    scopus 로고
    • The atomic numbering is based on thebicylo[3.3.1]non-3-en-2-one core
    • The atomic numbering is based on thebicylo[3.3.1]non-3-en-2-one core.
  • 79
    • 84925571786 scopus 로고    scopus 로고
    • The diastereomer mixture was used for the next intramolecular Michael reaction without separation
    • The diastereomer mixture was used for the next intramolecular Michael reaction without separation.
  • 84
    • 84925571785 scopus 로고    scopus 로고
    • In the reduction of 7-endo-tert-butoxycarbonyl-1,5- dimethylbicyclo[3.3.1]-non-2-en-9-one with NaBH4, practically no diastereoselectivity was observed dr 44:56
    • 4, practically no diastereoselectivity was observed (dr 44:56).
  • 87
    • 84925564612 scopus 로고    scopus 로고
    • In initial studies, the C7-tert-butoxy ester was used as the substituent. However, the organocerium reaction did not proceed with this ester. Therefore, the less bulky ethyl ester 3 was used instead for the ensuing synthetic studies.
    • In initial studies, the C7-tert-butoxy ester was used as the substituent. However, the organocerium reaction did not proceed with this ester. Therefore, the less bulky ethyl ester 3 was used instead for the ensuing synthetic studies.
  • 94
    • 84925571784 scopus 로고    scopus 로고
    • The product could not be freed of small quanitities of impurities upon purification. Therefore, the product was used for the next reaction after only simple purification
    • The product could not be freed of small quanitities of impurities upon purification. Therefore, the product was used for the next reaction after only simple purification.
  • 97
    • 84925564611 scopus 로고    scopus 로고
    • 1H NMR of the crude product, which was obtained from the reaction in toluene, some complicated signals were observed in the aromatic region.
    • 1H NMR of the crude product, which was obtained from the reaction in toluene, some complicated signals were observed in the aromatic region.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.