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Total syntheses or formal total syntheses of (±)-lycorine: (a) Tsuda, Y.; Sano, T.; Taga, J.; Isobe, K.; Toda, J.; Irie, H.; Tanaka, H.; Takagi, S.; Yamaki, M.; Murata, M. J. Chem. Soc., Chem. Commun. 1975, 933.
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Total synthesis of (+)- or (-)-lycorine: (a) Schultz, A. G.; Holoboski, M. A.; Smyth, M. S. J. Am. Chem. Soc. 1996, 118, 6210. [(+)-lycorine].
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Total synthesis of (+)- or (-)-lycorine: (a) Schultz, A. G.; Holoboski, M. A.; Smyth, M. S. J. Am. Chem. Soc. 1996, 118, 6210. [(+)-lycorine].
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lycorine
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Compound 3 can be obtained from the Aldrich Chemical Co. (Catalogue Number 489492) or from Questor, Queen's University of Belfast, Northern Ireland. Questor Centre Contact Page: http://questor.qub.ac.uk/ newsite/contact.htm (accessed July 2, 2009). For reviews on methods for generating cis-1,2-dihydrocatechols by microbial dihydroxylation of the corresponding aromatics, as well as the synthetic applications of these metabolites, see: (a) Hudlicky, T.; Gonzalez, D.; Gibson, D. T. Aldrichimica Acta 1999, 32, 35.
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Compound 3 can be obtained from the Aldrich Chemical Co. (Catalogue Number 489492) or from Questor, Queen's University of Belfast, Northern Ireland. Questor Centre Contact Page: http://questor.qub.ac.uk/ newsite/contact.htm (accessed July 2, 2009). For reviews on methods for generating cis-1,2-dihydrocatechols by microbial dihydroxylation of the corresponding aromatics, as well as the synthetic applications of these metabolites, see: (a) Hudlicky, T.; Gonzalez, D.; Gibson, D. T. Aldrichimica Acta 1999, 32, 35.
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For related examples of this type of epoxide ring-opening process, see
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For related examples of this type of epoxide ring-opening process, see: Banwell, M. G.; Haddad, N.; Hudlicky, T.; Nugent, T. C.; Mackay, M. F.; Richards, S. L. J. Chem. Soc., Perkin Trans. 1 1997, 1779.
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In keeping with expectations (Chaumeil, H.; Signorella, S.; Le Drian, C Tetrahedron 2000, 56, 9655) the 2,2-dimethyl-l,3- propanediol derived boronate 9, which was readily prepared by the methods defined in the Supporting Information, proved a more effective coupling partner than its pinacol-derived equivalent
-
In keeping with expectations (Chaumeil, H.; Signorella, S.; Le Drian, C Tetrahedron 2000, 56, 9655) the 2,2-dimethyl-l,3- propanediol derived boronate 9, which was readily prepared by the methods defined in the Supporting Information, proved a more effective coupling partner than its pinacol-derived equivalent
-
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42
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34548529509
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42149195294
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For a related reduction process involving Raney-cobalt see
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For a related reduction process involving Raney-cobalt see: Janey, J. M.; Orella, C. J.; Njolito, E.; Baxter, J. M.; Rosen, J. D.; Palucki, M.; Sidler, R. R.; Li, W.; Kowal, J. J.; Davies, I. W. J. Org. Chem. 2008, 73, 3212.
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Li, W.8
Kowal, J.J.9
Davies, I.W.10
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44
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49149145492
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