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.

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Abstract
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
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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.
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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