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Volumn 51, Issue 58, 2015, Pages 11568-11571

Construction of the [6-7-5-5] tetracyclic core of all the carbocyclic frameworks of yuzurimine-type alkaloids

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKALOID DERIVATIVE; ALKENE; CARBOXYLIC ACID; HYDROXYL GROUP; UNCLASSIFIED DRUG; YUZURIMINE TYPE ALKALOID; ALKALOID;

EID: 84936139186     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c5cc03479e     Document Type: Article
Times cited : (18)

References (38)
  • 30
    • 84985570392 scopus 로고
    • We could not get the fully substituted enol triflate even under thermodynamic conditions. Preliminary calculation of a simpler model bicyclic enol triflate suggested that the less-substituted enol triflate in 16 is more stable than the fully substituted one. In the tricyclic [7-5-5] system, the tetrasubstituted olefin in 4 is suggested to be less stable than the trisubstituted olefin. However, the energy difference is smaller than in the bicyclic system. We would have a chance of isomerization into the desired isomer after the construction of [7-5-5] or [6-7-5-5] carbocyclic skeleton. Currently, we are examining the isomerization of the double bond from the C10-C17 to the C9-C10 for the synthesis of yuzurimine-type alkaloids
    • J. K. Stille Angew. Chem., Int. Ed. Engl. 1986 25 508
    • (1986) Angew. Chem., Int. Ed. Engl. , vol.25 , pp. 508
    • Stille, J.K.1
  • 37
    • 80053084413 scopus 로고    scopus 로고
    • Tetracyclic compound 28 contains a small amount of impurities. The yield of 29 was calculated from 26 The structures of lactone 27 and tetracyclic compound 28 were determined by analysis of 2D NMR spectra. The stereochemistry of the tetracyclic compound 28 was established by NOESY correlations of acetate 29 (see the ESI)
    • J. Y. Cha J. T. S. Yeoman S. E. Reisman J. Am. Chem. Soc. 2011 133 14964
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 14964
    • Cha, J.Y.1    Yeoman, J.T.S.2    Reisman, S.E.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.