Convergent synthesis of naphthylisoquinoline alkaloids: Total synthesis of (+)-O-methylancistrocline

Journal of Organic Chemistry

Volumn 61, Issue 20, 1996, Pages 7101-7105

  Chau, Phung ^a   Czuba, Ivona R ^a   Rizzacasa, Mark A ^a   Bringmann, Gerhard ^b   Gulden, Klaus Peter ^b   Schäffer, Manuela ^b  

^a UNIVERSITY OF MELBOURNE   (Australia)

^b Inst F Org Chem der Univ   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ISOQUINOLINE DERIVATIVE; O METHYLANCISTROCLINE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029805585     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9607119     Document Type: Article

References (47)

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15. Recent examples include: Aryl imines (with chiral catalyst): Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732. Chiral sulfoxides: Baker, R. W.; Pocock, G. R.; Sargent, M. V.; Twiss, E. Tetrahedron Asymmetry 1993, 4, 2423. 2-Menthoxybenzoates: Miyano, S.; Koike, N.; Hattori, T. J. Chem. Soc., Perkin Trans, 1 1994, 2273. Planar chiral tricarbonyl(arene)chromium complexes: Uemura, M.; Watanabe, T.; Kamikawa, K. J. Org. Chem. 1998, 61, 1375.
16. Recent examples include: Aryl imines (with chiral catalyst): Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732. Chiral sulfoxides: Baker, R. W.; Pocock, G. R.; Sargent, M. V.; Twiss, E. Tetrahedron Asymmetry 1993, 4, 2423. 2-Menthoxybenzoates: Miyano, S.; Koike, N.; Hattori, T. J. Chem. Soc., Perkin Trans, 1 1994, 2273. Planar chiral tricarbonyl(arene)chromium complexes: Uemura, M.; Watanabe, T.; Kamikawa, K. J. Org. Chem. 1998, 61, 1375.
17. Recent examples include: Aryl imines (with chiral catalyst): Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732. Chiral sulfoxides: Baker, R. W.; Pocock, G. R.; Sargent, M. V.; Twiss, E. Tetrahedron Asymmetry 1993, 4, 2423. 2-Menthoxybenzoates: Miyano, S.; Koike, N.; Hattori, T. J. Chem. Soc., Perkin Trans, 1 1994, 2273. Planar chiral tricarbonyl(arene)chromium complexes: Uemura, M.; Watanabe, T.; Kamikawa, K. J. Org. Chem. 1998, 61, 1375.
18. Recent examples include: Aryl imines (with chiral catalyst): Shindo, M.; Koga, K.; Tomioka, K. J. Am. Chem. Soc. 1992, 114, 8732. Chiral sulfoxides: Baker, R. W.; Pocock, G. R.; Sargent, M. V.; Twiss, E. Tetrahedron Asymmetry 1993, 4, 2423. 2-Menthoxybenzoates: Miyano, S.; Koike, N.; Hattori, T. J. Chem. Soc., Perkin Trans, 1 1994, 2273. Planar chiral tricarbonyl(arene)chromium complexes: Uemura, M.; Watanabe, T.; Kamikawa, K. J. Org. Chem. 1998, 61, 1375.
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24. Meyers, A. I.; Lutomski, K. A. J. Am. Chem. Soc. 1982, 104, 879. Meyers, A. I.; Himmelsbach, R. J. J. Am. Chem. Soc. 1985, 107, 682. Meyers, A. I.; Flisak, J. R.; Aitken, R. A. J. Am. Chem. Soc. 1987, 109, 5446. Warshawsky, A. M.; Meyers, A. I. J. Am. Chem. Soc. 1990, 112, 8090. Meyers, A. I.; Meier, A.; Rawson, D. J. Tetrahedron Lett. 1992, 33, 853. For a comprehensive account on the chemistry of 2-oxazolines see: Gant, J. G.; Meyers, A. I. Tetrahedron 1994, 2291.
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46. Rauhut, G.; Chandrasekhar, J.; Alex, A.; Beck, B.; Sauer, W.; Clark, T.; VAMP 5.5, available from Oxford Molecular Limited, The Magdalen Centre, Oxford Science Park, Sandford on Thames, Oxford OX4 4GA, England.
47. The CD programs used, BDZDO and MCD3SP, were written by J. Downing and J. Michl (University of Colorado at Bolder), modified by J. Fleischhauer, W. Schleker, and B. Kramer (RWTH Aachen), and ported to LinuX by K.-P. Gulden (University of Würzburg).