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Volumn 64, Issue 35, 2008, Pages 8052-8058

First asymmetric synthesis of pyrrolizidine alkaloids, (+)-hyacinthacine B1 and (+)-B2

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; HYACINTHACINE B1; HYACINTHACINE B2; PYRROLIZIDINE ALKALOID;

EID: 47049117544     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.06.078     Document Type: Article
Times cited : (36)

References (64)
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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
  • 54
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    • The reaction of 6 with Grignard reagent was undesirably accompanied with the formation of the corresponding N-H lactam derived from Boc-elimination, see:
    • The reaction of 6 with Grignard reagent was undesirably accompanied with the formation of the corresponding N-H lactam derived from Boc-elimination, see:. Ginovannini A., Savoia D., and Umani-Ronchi A. J. Org. Chem 54 (1989) 228
    • (1989) J. Org. Chem , vol.54 , pp. 228
    • Ginovannini, A.1    Savoia, D.2    Umani-Ronchi, A.3
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    • note
    • 1H NMR analysis as shown in the text.
  • 56
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    • note
    • 3 to the carbonyl oxygen in a dilute EtOH solution.
  • 57
    • 47049122536 scopus 로고    scopus 로고
    • note
    • 12a On the other hand, in order to determine the absolute configurations of ia and ib, those were independently converted to iiia and iiib and estimated to have the depicted stereochemistries, respectively, based on its symmetrically spectral data of iiib.
  • 58
    • 47049105875 scopus 로고    scopus 로고
    • note
    • Intrigued by hitherto known procedures such as in acidic media regarding the Boc-elimination, where an inseparable mixture was obtained due to the presence of the acid-labile acetonide group, we investigated an alternative method and were surprised to find that NaH could effect prominently to eliminate the Boc function smoothly after desilylation of 8a, finally leading to the desired Cbz-containing substrate 9. It is of great importance to note that the Boc-elimination with NaH in this case requires the presence of the neighboring hydroxyl group. The reason for such an unusual elimination reaction has not been yet clarified.
  • 62
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    • 4-catalyzed dihydroxylation reactions carried out on 9 gave the non-stereoselective results
    • 4-catalyzed dihydroxylation reactions carried out on 9 gave the non-stereoselective results
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 2801
    • Takahata, H.1    Kubota, M.2    Momose, T.3
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    • note
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    • 13C NMR spectra was observed. It is, however, generally known that variation in solvent (ionic strength, hydrogen bonding, metal ion chelation) can exert discrepancies in NMR spectra of polyhydroxylated alkaloids, see:
    • 13C NMR spectra was observed. It is, however, generally known that variation in solvent (ionic strength, hydrogen bonding, metal ion chelation) can exert discrepancies in NMR spectra of polyhydroxylated alkaloids, see:. Wormald M.R., Nash R.J., Hrnciar P., White J.D., Molyneux R.J., and Fleet G.W.J. Tetrahedron: Asymmetry 9 (1998) 2549
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 2549
    • Wormald, M.R.1    Nash, R.J.2    Hrnciar, P.3    White, J.D.4    Molyneux, R.J.5    Fleet, G.W.J.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.