Stereoselective Synthesis of Benzylated Prodelphinidins and Their Diastereomers with Use of the Mitsunobu Reaction in the Preparation of Their Gallocatechin Precursors
Krohn K, Ahmed I, John M, Letzel M, Kuck D (2010)
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2010(13): 2544-2554.
Zeitschriftenaufsatz
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Autor*in
Krohn, Karsten;
Ahmed, Ishtiaq;
John, Markus;
Letzel, MatthiasUniBi;
Kuck, DietmarUniBi
Abstract / Bemerkung
The tetrabenzylated catechin 9 was prepared by benzylation of the commercially available pure (+)-catechin (3) and coupled with the commercially unavailable pentabenzylated (-)-gallocatechin 10, prepared in a one-step Mitsunobu-type cyclization of the triol 8 The highly stereoselective synthesis of benzylated prodelphinidins - catechin-(4 alpha -> 8)-gallocatechin (13), gallocatechin-(4 alpha -> 8)-gallocatechin (14), and gallocatechin-(4 alpha -> 8)-catechin (15) - is reported for the first time. The ESI(+)-CID mass spectra of the coupling products were found to feature regioselective retro-Diels-Alder (RDA) reactions and unusual sequential losses of pairs of C7H7 radicals (182 u) from the Na+ adduct ions
Stichworte
Natural products;
Polyphenols;
Flavanoids;
C-C coupling;
Phytochemistry
Erscheinungsjahr
2010
Zeitschriftentitel
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Band
2010
Ausgabe
13
Seite(n)
2544-2554
ISSN
1434-193X
eISSN
1099-0690
Page URI
https://pub.uni-bielefeld.de/record/1795835
Zitieren
Krohn K, Ahmed I, John M, Letzel M, Kuck D. Stereoselective Synthesis of Benzylated Prodelphinidins and Their Diastereomers with Use of the Mitsunobu Reaction in the Preparation of Their Gallocatechin Precursors. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2010;2010(13):2544-2554.
Krohn, K., Ahmed, I., John, M., Letzel, M., & Kuck, D. (2010). Stereoselective Synthesis of Benzylated Prodelphinidins and Their Diastereomers with Use of the Mitsunobu Reaction in the Preparation of Their Gallocatechin Precursors. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010(13), 2544-2554. https://doi.org/10.1002/ejoc.201000053
Krohn, Karsten, Ahmed, Ishtiaq, John, Markus, Letzel, Matthias, and Kuck, Dietmar. 2010. “Stereoselective Synthesis of Benzylated Prodelphinidins and Their Diastereomers with Use of the Mitsunobu Reaction in the Preparation of Their Gallocatechin Precursors”. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2010 (13): 2544-2554.
Krohn, K., Ahmed, I., John, M., Letzel, M., and Kuck, D. (2010). Stereoselective Synthesis of Benzylated Prodelphinidins and Their Diastereomers with Use of the Mitsunobu Reaction in the Preparation of Their Gallocatechin Precursors. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2010, 2544-2554.
Krohn, K., et al., 2010. Stereoselective Synthesis of Benzylated Prodelphinidins and Their Diastereomers with Use of the Mitsunobu Reaction in the Preparation of Their Gallocatechin Precursors. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010(13), p 2544-2554.
K. Krohn, et al., “Stereoselective Synthesis of Benzylated Prodelphinidins and Their Diastereomers with Use of the Mitsunobu Reaction in the Preparation of Their Gallocatechin Precursors”, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2010, 2010, pp. 2544-2554.
Krohn, K., Ahmed, I., John, M., Letzel, M., Kuck, D.: Stereoselective Synthesis of Benzylated Prodelphinidins and Their Diastereomers with Use of the Mitsunobu Reaction in the Preparation of Their Gallocatechin Precursors. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2010, 2544-2554 (2010).
Krohn, Karsten, Ahmed, Ishtiaq, John, Markus, Letzel, Matthias, and Kuck, Dietmar. “Stereoselective Synthesis of Benzylated Prodelphinidins and Their Diastereomers with Use of the Mitsunobu Reaction in the Preparation of Their Gallocatechin Precursors”. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2010.13 (2010): 2544-2554.
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