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Volumn 64, Issue 22, 2008, Pages 5254-5261

New asymmetric strategy for the total synthesis of naturally occurring (+)-alexine and (-)-7-epi-alexine

Author keywords

[No Author keywords available]

Indexed keywords

7 EPI ALEXINE; ALEXINE; ALKALOID; AUSTRALINE; CASUARINE; DIHYDROXYHELIOTRIDANE; GLYCOSIDASE INHIBITOR; NATURAL PRODUCT; PYRROLIDINE DERIVATIVE; PYRROLIZIDINE ALKALOID;

EID: 42749089287     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.03.029     Document Type: Article
Times cited : (23)

References (65)
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    • Fellows, L. E.; Nash, R. J. PCT Int. Appl. WO GB Apple. 7,951, 1989 (Appl. No. PCT/GB1990/000538);
    • Fellows, L. E.; Nash, R. J. PCT Int. Appl. WO GB Apple. 7,951, 1989 (Appl. No. PCT/GB1990/000538);
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    • Recently, the search in the same group for hyacinthacines in the Hyacinthaceae has led to the isolation from Scilla socialis bulbs of new 11 hyacinthacines, see: and references cited therein
    • Recently, the search in the same group for hyacinthacines in the Hyacinthaceae has led to the isolation from Scilla socialis bulbs of new 11 hyacinthacines, see:. Kato A., Kato N., Adachi I., Hollinshead J., Fleet G.W.J., Kuriyama C., Ikeda K., Asano N., and Nash R.J. J. Nat. Prod. 70 (2007) 993 and references cited therein
    • (2007) J. Nat. Prod. , vol.70 , pp. 993
    • Kato, A.1    Kato, N.2    Adachi, I.3    Hollinshead, J.4    Fleet, G.W.J.5    Kuriyama, C.6    Ikeda, K.7    Asano, N.8    Nash, R.J.9
  • 28
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    • Recent syntheses:
    • Recent syntheses:
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    • 16d-f for the synthesis of glycosidase or glycosyltransferase inhibitors.
    • 16d-f for the synthesis of glycosidase or glycosyltransferase inhibitors.
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    • The absolute configuration of the newly created stereogenic center of 8 was easily characterized to be S after derivatization to the corresponding vinyl lactam 18 as shown below.{A figure is presented}
    • The absolute configuration of the newly created stereogenic center of 8 was easily characterized to be S after derivatization to the corresponding vinyl lactam 18 as shown below.{A figure is presented}
  • 59
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    • 16a,b
    • 16a,b
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    • note
    • Initially we investigated the direct pyrrolizidine ring formation employing the N-benzylated derivative of 15a via the quaternary ammonium salt, however, these reactions resulted in the formation of a complex mixture including N-mesylated compounds and gave the desired product 16a in very low yield (10∼15%).
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    • note
    • 4b after completion of the synthesis of 7-epi-alexine 1a.
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    • The same type of transition metal halide-promoted six-membered chelating reactions have been already demonstrated in this laboratory with high stereoselectivity, see:
    • The same type of transition metal halide-promoted six-membered chelating reactions have been already demonstrated in this laboratory with high stereoselectivity, see:. Yoda H., Nakajima T., and Takabe K. Tetrahedron Lett. 37 (1996) 5531
    • (1996) Tetrahedron Lett. , vol.37 , pp. 5531
    • Yoda, H.1    Nakajima, T.2    Takabe, K.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.