Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 38, Pages 10129-10133Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201405600
Keywords
annulation; heterocylces; natural products; structure elucidation; total synthesis
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Funding
- JSPS [23000006]
- Grants-in-Aid for Scientific Research [23000006] Funding Source: KAKEN
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The first stereoselective syntheses of doubly linked (A-type) oligocatechins, (+)-procyanidin A(2) and (+)-cinnamtannin B-1, have been achieved. Ethylenedioxy-bridged flavans served as excellent platforms, thus allowing annulation with nucleophilic catechin units in a stereoselective manner. An additional key was the new synthetic approach to selectively protected nucleophilic catechin, thus enabling regioselective construction of the key dioxabicyclo skeleton of the A-type oligocatechins.
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