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Enantioselective Synthesis of Some Tetracyclic Isoquinoline Alkaloids by Asymmetric Transfer Hydrogenation Catalysed by a Chiral Ruthenium Complex

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Summary.

Asymmetric transfer hydrogenation catalysed by chiral ruthenium complexes was the method for enantioselective synthesis of (R)-(+)-coralydine, (S)-(−)-homoprotoberberine, and (S)-(+)-homoaporphine in fair to excellent enantiomeric purity.

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References

  • Phillipson JD, Roberts MF, Zenk MH (eds) (1985) The Chemistry and Biology of Isoquinoline Alkaloids. Springer, New York

  • Phillipson JD, Zenk MH (eds) (1980) Indole and Biogenetically Related Alkaloids. Academic Press, London

  • MD Rozwadowska (1994) Heterocycles 39 903

    Google Scholar 

  • M Chrzanowska MD Rozwadowska (2004) Chem Rev 104 3341 Occurrence Handle10.1021/cr030692k Occurrence Handle15250744

    Article  PubMed  Google Scholar 

  • D Makhey B Gatto C Yu A Liu LF Liu EJ LaVoie (1996) Bioorgan Med Chem 4 781 Occurrence Handle10.1016/0968-0896(96)00054-5

    Article  Google Scholar 

  • N Sotomayor E Dominguez E Lete (1996) J Org Chem 61 4062 Occurrence Handle10.1021/jo960007s Occurrence Handle11667284

    Article  PubMed  Google Scholar 

  • AR Hajipour M Hantehzadeh (1999) J Org Chem 64 8475 Occurrence Handle10.1021/jo990267k

    Article  Google Scholar 

  • N Uematsu A Fujii S Hashiguchi T Ikariya R Noyori (1996) J Am Chem Soc 118 4916 Occurrence Handle10.1021/ja960364k

    Article  Google Scholar 

  • Z Czarnocki DB MacLean WA Szarek (1986) Bull Soc Chim Belg 95 749

    Google Scholar 

  • A Brossi J Van Burik S Teitel (1968) Helv Chim Acta 51 1965 Occurrence Handle10.1002/hlca.19680510816 Occurrence Handle5760865

    Article  PubMed  Google Scholar 

  • A Brossi S Teitel (1969) Helv Chim Acta 52 1228 Occurrence Handle10.1002/hlca.19690520508

    Article  Google Scholar 

  • Z Czarnocki DB MacLean WA Szarek (1987) Can J Chem 65 2356

    Google Scholar 

  • Z Czarnocki JB Mieczkowski M Ziółkowski (1996) Tetrahedron Asymm 7 2711 Occurrence Handle10.1016/0957-4166(96)00349-7

    Article  Google Scholar 

  • LF Tietze Y Zhou E Töpken (2000) Eur J Org Chem 12 2247 Occurrence Handle10.1002/1099-0690(200006)2000:12<2247::AID-EJOC2247>3.0.CO;2-4

    Article  Google Scholar 

  • H Bruderer J Metzger A Brossi JJ Daly (1976) Helv Chim Acta 59 2793 Occurrence Handle10.1002/hlca.19760590818

    Article  Google Scholar 

  • T Itoh K Nagata M Yokoya M Miyazaki K Kameoka S Nakamura A Ohsawa (2003) Chem Pharm Bull 51 951 Occurrence Handle10.1248/cpb.51.951 Occurrence Handle12913234

    Article  PubMed  Google Scholar 

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Authors and Affiliations

  1. Faculty of Chemistry, Warsaw University, 02-093, Warsaw, Poland

    Joanna Szawkało & Zbigniew Czarnocki

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  1. Joanna Szawkało
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  2. Zbigniew Czarnocki
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Correspondence to Zbigniew Czarnocki.

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Szawkało, J., Czarnocki, Z. Enantioselective Synthesis of Some Tetracyclic Isoquinoline Alkaloids by Asymmetric Transfer Hydrogenation Catalysed by a Chiral Ruthenium Complex. Monatsh. Chem. 136, 1619–1627 (2005). https://doi.org/10.1007/s00706-005-0341-8

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  • DOI: https://doi.org/10.1007/s00706-005-0341-8

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