Abstract:
Treatment of 6β-chloro-6-deoxycodeine 1 with Pd(PPh3)4 yields 6-demethoxythebaine 2 and the π-allylic palladium complex 3, which further reacts with RZnX to give the cross-coupling product of the allylic ligand and R (compounds 5 and 6, respectively). The same products are formed upon reaction of 6β-chloro-6-deoxycodeine 1 with RZnX in the presence of catalytic amounts of Pd(PPh3)4.
Document Type:
Article
Language: English
Citation:
V. N. Kalinin, I. L. Belyakova, V. V. Derunov, J. K. Park, H. Schmidhammer, “Synthesis and Properties of π-Complexes of Morphine Alkaloids with Palladium”, Mendeleev Commun., 5:1 (1995), 22–23
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https://www.mathnet.ru/eng/mendc/v5/i1/p22
This publication is cited in the following 8 articles:
Thomas Erhard, Gunnar Ehrlich, Peter Metz, “Eine Totalsynthese von (±)‐Codein durch 1,3‐dipolare Cycloaddition”, Angewandte Chemie, 123:17 (2011), 3979
Thomas Erhard, Gunnar Ehrlich, Peter Metz, “A Total Synthesis of (±)‐Codeine by 1,3‐Dipolar Cycloaddition”, Angew Chem Int Ed, 50:17 (2011), 3892
P. Espinet, A.C. Albéniz, Comprehensive Organometallic Chemistry III, 2007, 315
Alexandr Jegorov, Hana Petříčková, Bohumil Kratochvíl, Ivana Císařová, “An Unusual cis-Dichloro[17-(cyclobutylmethyl)-3-methoxymorphinan-14-ol-N,O]palladium(II) Complex”, Collect. Czech. Chem. Commun., 71:3 (2006), 434
Ryo Ikegami, Akiko Koresawa, Takanori Shibata, Kentaro Takagi, “Functionalized Arylzinc Compounds in Ethereal Solvent: Direct Synthesis from Aryl Iodides and Zinc Powder and Application to Pd-Catalyzed Reaction with Allylic Halides”, J. Org. Chem., 68:6 (2003), 2195
Gerhard Laus, Johannes Schütz, Herwig Schottenberger, Max Andre, Klaus Wurst, Mariana Spetea, Karl‐Hans Ongania, Adrian G. Müller, Helmut Schmidhammer, “Etorphine‐Related Ferrocenyl‐Substituted Morphinan Alkaloids”, Helvetica Chimica Acta, 86:10 (2003), 3274
K. W. Bentley, “β-Phenylethylamines and the isoquinoline alkaloids”, Nat. Prod. Rep., 13:2 (1996), 127
V. N. Kalinin, V. V. Derunov, L. Maat, J. K. Park, H. Schmidhammer, “Synthesis of π-Complexes of Codeine with Iron and Molybdenum”, Mendeleev Commun., 5:6 (1995), 222–223
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