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Volumn 13, Issue 15, 2011, Pages 3988-3991

Total syntheses of (-) epilupinine and (-)-tashiromine using imino-aldol reactions

Author keywords

[No Author keywords available]

Indexed keywords

3-HYDROXYBUTANAL; ALDEHYDE; ALDOL; DRUG DERIVATIVE; IMINE; INDOLIZINE DERIVATIVE; LUPININE; SPARTEINE; TASHIROMINE;

EID: 79961034481     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2015048     Document Type: Article
Times cited : (44)

References (43)
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  • 4
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    • For the epimerization of lupinine to epilupinine
    • For the epimerization of lupinine to epilupinine: Winterfeld, K.; Holschneider, F. W. Chem. Ber. 1931, 64, 137-150
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    • For selected asymmetric total syntheses of tashiromine, see ref 6a and
    • For selected asymmetric total syntheses of tashiromine, see ref 6a and: Gage, J. L.; Branchaud, B. P. Tetrahedron Lett. 1997, 38, 7007-7010
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  • 21
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    • For selected examples of syntheses of racemic epilupinine
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    • For selected syntheses of racemic tashiromine, see ref 8d,8f and
    • For selected syntheses of racemic tashiromine, see ref 8d,8f and: Pandey, G.; Lakshmaiah, G. Tetrahedron Lett. 1993, 34, 4861-4864
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    • For examples of imino-aldol reactions of aryl N -sulfinyl imines
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  • 36
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    • For some sequences involving additions of organometallic species to tert -butylsulfinyl imines followed by cyclization
    • For some sequences involving additions of organometallic species to tert -butylsulfinyl imines followed by cyclization: Voituriez, A.; Ferreira, F.; Pérez-Luna, A.; Chemla, F. Org. Lett. 2007, 9, 4705-4708
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    • For an example using p -tolylsulfinyl imines:;; Synthesis 2006, 687-691
    • Reddy, L. R.; Prashad, M. Chem. Commun. 2010, 46, 222-224 For an example using p -tolylsulfinyl imines: Ruano, J. L. G.; Aleman, J.; Cid, M. B. Synthesis 2006, 687-691
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    • 2 t -Bu, was isolated after prolonged reaction times for the formation of sulfinyl imines. The structure was confirmed by X-ray crystallography. For the formation of a similar compound, see
    • 2 t -Bu, was isolated after prolonged reaction times for the formation of sulfinyl imines. The structure was confirmed by X-ray crystallography. For the formation of a similar compound, see: Drabowicz, J. Heteroat. Chem. 2002, 13, 437-442
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    • For an example of a prionate imino-aldol reaction with a functionalized tert -butylsulfinyl imine
    • For an example of a prionate imino-aldol reaction with a functionalized tert -butylsulfinyl imine: Wen, S. J.; Carey, K. L.; Nakao, Y.; Fusetani, N.; Packham, G.; Ganesan, A. Org. Lett. 2007, 9, 1105-1108
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  • 43
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    • Davis and Xu have recently reported that anti imino aldol products can be obtained by diastereoselective alkylation of acetate imino-aldol adducts
    • Davis and Xu have recently reported that anti imino aldol products can be obtained by diastereoselective alkylation of acetate imino-aldol adducts: Davis, F. A.; Xu, P. J. Org. Chem. 2011, 76, 3329-3337
    • (2011) J. Org. Chem. , vol.76 , pp. 3329-3337
    • Davis, F.A.1    Xu, P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.