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Volumn 69, Issue 46, 2013, Pages 9826-9831

Convenient synthesis of epimeric indolizidines by the intramolecular 1,3-dipolar cycloaddition of a sugar derived N-(3-alkenyl)nitrone

Author keywords

1,3 dipolar cycloaddition; Intramolecular; Polyhydroxylated indolizidines; Stereoselective reduction; Sugar nitrones

Indexed keywords

(1',2':4',5' DI ISOPROPYLIDENE 1',2',3',4',5' PENTAHYDROXYPENTYL) 2,2 DIMETHYL 7 OXA 1 AZABICYCLO[2.2.1]HEPTANE; (1,2 DIHYDROXYETHYL) 5,5 DIMETHYLINDOLIZIDIN 1,2,7 TRIOL; (1,2 O ISOPROPYLIDENE 1,2 DIHYDROXYETHYL) 1,2 DIHYDROXYTHYL) 1,2 O ISOPROPYLIDENE 1,2 DIHYDROXY 5,5 DIMETHYLINDOLIZIDIN 7 ONE; (1,2 O ISOPROPYLIDENE 1,2 DIHYDROXYETHYL) 1,2 O ISOPROPYLIDENE 5,5 DIMETHYLINDOLIZIDIN 1,2,7 TRIOL; (ISOPROPYLIDENE 1,2 DIHYDROXYETHYL) 1,2 O ISOPROPYLIDENE 5,5 DIMETHYLINDOLIZIDIN 1,2,7 TRIOL; AMMONIA; INDOLIZIDINE DERIVATIVE; N (3 ALKENYL)NITRONE; NITRONE DERIVATIVE; SODIUM AZIDE; UNCLASSIFIED DRUG;

EID: 84885174184     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.09.008     Document Type: Article
Times cited : (16)

References (100)
  • 15
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    • For the synthesis of indolizidines from azasugar derived nitrones, see
    • For the synthesis of indolizidines from azasugar derived nitrones, see: X. Li, Z. Zhu, K. Duan, H. Chen, Z. Li, Z. Li, and P. Zhang Tetrahedron 65 2009 2322
    • (2009) Tetrahedron , vol.65 , pp. 2322
    • Li, X.1    Zhu, Z.2    Duan, K.3    Chen, H.4    Li, Z.5    Li, Z.6    Zhang, P.7
  • 90
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    • The use of bases reported in the literature () resulted in formation of a complex mixture
    • The use of bases reported in the literature (F.M. Cordero, F. Machetti, F. De Sarlo, and A. Brandi Gazz. Chim. Ital. 127 1997 25) resulted in formation of a complex mixture
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    • The bulky nucleophiles such L-Selectride prefer equatorial approach. The transition state for equatorial attack of the hydride reagent is less sterically hindered and lower in energy. The transition state for axial approach suffers from 1,3-diaxial interaction (M. Harmata, University of Missouri Columbia Chapter 10)
    • The bulky nucleophiles such L-Selectride prefer equatorial approach. The transition state for equatorial attack of the hydride reagent is less sterically hindered and lower in energy. The transition state for axial approach suffers from 1,3-diaxial interaction (R. Bruckner M. Harmata, Organic Mechanisms. Reactions, Stereochemistry and Synthesis 2010 University of Missouri Columbia 397 455 Chapter 10)
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    • Bruckner, R.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.