Annulation Approach to Doubly Linked (A‐type) Oligocatechins: Syntheses of (+)‐Procyanidin A2 and (+)‐Cinnamtannin B11. Issue 38 (28th July 2014)

• Record Type: Journal Article
• Authors: Ito, Yuji; Ohmori, Ken; Suzuki, Keisuke
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 38(2014)
• Page Start: 10129
• Page End: 10133
• Publication Date: 2014-07-28
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201405600
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The first stereoselective syntheses of doubly linked (A‐type) oligocatechins, (+)‐procyanidin A₂ and (+)‐cinnamtannin B₁, 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.</p> </abstract>