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Volumn 73, Issue 14, 2008, Pages 5287-5297

Efficient conversion of carbohydrates into 1-C-alditols: Application to the synthesis of chiral γ-substituted butenolides and bicyclic alkaloid analogues

Author keywords

[No Author keywords available]

Indexed keywords

BIOMOLECULES; CARBOHYDRATES; CHEMICAL REACTIONS; ORGANIC COMPOUNDS; STEREOSELECTIVITY; SUGAR (SUCROSE); SUGARS;

EID: 48249097470     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800478a     Document Type: Article
Times cited : (12)

References (69)
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    • For the preliminary communications on this work, see: (a) Boto, A.; Hernández, D.; Hernández, R. Org. Lett. 2007, 9, 1721-1724.
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    • For instance, the coupling of commercial 2-trimethylsilyloxyfuran (TMSOF) with aldehydes is a remarkable strategy for butenolide synthesis Maulide, N.; Marko, I. E. Org. Lett. 2006, 8, 3705-3707.
    • (a) For instance, the coupling of commercial 2-trimethylsilyloxyfuran (TMSOF) with aldehydes is a remarkable strategy for butenolide synthesis Maulide, N.; Marko, I. E. Org. Lett. 2006, 8, 3705-3707.
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    • Compound 17 was volatile, and loss of weight was observed under vacuum.
    • Compound 17 was volatile, and loss of weight was observed under vacuum.
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    • For related allyl systems and their synthetic applications, see: a
    • For related allyl systems and their synthetic applications, see: (a) Lievens, S. C.; Molinski, T. F. J. Am. Chem. Soc. 2006, 128, 11764-11765.
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    • The numbering shown on the C-alditol figures does not always match the IUPAC rules. However, this numbering system allows an easier discussion of the results: the polyhydroxylated chain is numbered as the acetoxy acetal precursor, and the new allyl or alkyl chain is numbered starting from the position closer to the polyol unit
    • The numbering shown on the C-alditol figures does not always match the IUPAC rules. However, this numbering system allows an easier discussion of the results: the polyhydroxylated chain is numbered as the acetoxy acetal precursor, and the new allyl or alkyl chain is numbered starting from the position closer to the polyol unit.
  • 39
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    • Substrate 22 was previously reported: Kapoor, V. P. Indian J. Chem. 1973, 11, 13-16. However, our synthetic strategy differs from the previous version, and therefore, it is described in Supporting Information.
    • Substrate 22 was previously reported: Kapoor, V. P. Indian J. Chem. 1973, 11, 13-16. However, our synthetic strategy differs from the previous version, and therefore, it is described in Supporting Information.
  • 40
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    • NOESY experiments were carried out with compounds 21 and 26. The spatial interactions observed for compound 21 were 1-H (δH 4.63)/3-H (δH 5.43, 2-H (δH 4.28)/1′-Ha (δH 2.86, 2-H/1′-Hb (δH 3.06, Compound 26 showed the following spatial interactions: 1-H (δH 4.69)/3-H (δH 3.65, 1-H/4-H (δH 5.18, 2-H (δH 3.91)/1′-Ha (δH 3.16, 2-H/1′-Hb δH 3.49
    • H 3.49)
  • 41
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    • 1,2 = 4.0-6.0 Hz were obtained for the 1,2-trans and the 1,2-cis compounds, respectively.
    • 1,2 = 4.0-6.0 Hz were obtained for the 1,2-trans and the 1,2-cis compounds, respectively.
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    • and references therein
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    • H 1.5-2.5).
    • H 1.5-2.5).
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    • The experimental coupling constants matched theoretical ones, calculated as described in ref 18
    • (a) The experimental coupling constants matched theoretical ones, calculated as described in ref 18.
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    • For information on the Karplus-Altona equation, see
    • (b) For information on the Karplus-Altona equation, see: Haasnoot, C. A. G.; de Leeuw, F. A. A. M.; Altona, C. Tetrahedron 1980, 36, 2783-2792.
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    • 2,3 = 8.5-10.1 Hz for the 2,3-trans relationship.
    • 2,3 = 8.5-10.1 Hz for the 2,3-trans relationship.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.