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Volumn 56, Issue 8, 2017, Pages 2127-2131

Stereocontrolled Total Synthesis of (−)-Stemaphylline

Author keywords

boronic esters; lithiation borylation; Stemona alkaloids; stereocontrol; total synthesis

Indexed keywords

ALKALOIDS; AMINES; ESTERS;

EID: 85009773541     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201611273     Document Type: Article
Times cited : (63)

References (44)
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    • Building block 7 is commercially available but can be prepared in one step using the method developed by Whiting
    • Building block 7 is commercially available but can be prepared in one step using the method developed by Whiting: A. S. Batsanov, C. Grosjean, T. Schuetz, A. Whiting, J. Org. Chem. 2007, 72, 6276–6279.
    • (2007) J. Org. Chem. , vol.72 , pp. 6276-6279
    • Batsanov, A.S.1    Grosjean, C.2    Schuetz, T.3    Whiting, A.4
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    • Curiously, Whiting found that reaction of 2-Li-, N, -Boc-pyrrolidine with ClCH, B(pin) in the presence of ZnCl, gave the product in 69 % yield (Ref. [8]). In both cases, the same boronate complex is formed but reaction shown in Scheme 2 A is much less efficient
    • 2 gave the product in 69 % yield (Ref. [8]). In both cases, the same boronate complex is formed but reaction shown in Scheme 2 A is much less efficient.
  • 23
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    • on the migrating carbon is −0, when the N-Boc pyrrolidine is replaced by i-Pr, See the Supporting Information for full details of computational analysis
    • The natural charge (NBO) on the migrating carbon is −0.363 for the N-Boc pyrrolidine but substantially higher (−0.594) when the N-Boc pyrrolidine is replaced by i-Pr. See the Supporting Information for full details of computational analysis.
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    • Using Pd/C in the hydrogenation reaction resulted in the formation of a mixture of diastereoisomers of 3, presumably as a result of alkene isomerization prior to reduction, [2c] and references therein
    • Using Pd/C in the hydrogenation reaction resulted in the formation of a mixture of diastereoisomers of 3, presumably as a result of alkene isomerization prior to reduction. See Ref. [2c] and references therein.
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    • Attempts to convert iodide 25 into boronic ester 26 using copper catalysis as described by Ito and Marder were unsuccessful
    • Attempts to convert iodide 25 into boronic ester 26 using copper catalysis as described by Ito and Marder were unsuccessful. H. Ito, K. Kubota, Org. Lett. 2012, 14, 890–893;
    • (2012) Org. Lett. , vol.14 , pp. 890-893
    • Ito, H.1    Kubota, K.2
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    • Angew. Chem. 2012, 124, 543–547.
    • (2012) Angew. Chem. , vol.124 , pp. 543-547


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.