De Novo Synthesis of Furanose Sugars: Catalytic Asymmetric Synthesis of Apiose and Apiose‐Containing Oligosaccharides. Issue 33 (6th July 2016)

• Record Type: Journal Article
• Authors: Kim, Mijin; Kang, Soyeong; Rhee, Young Ho
• Is Part Of: Angewandte Chemie international edition. Volume 55:Issue 33(2016)
• Page Start: 9733
• Page End: 9737
• Publication Date: 2016-07-06
• Subjects: asymmetric synthesis -- carbohydrates -- de novo synthesis -- diastereoselectivity -- oligosaccharides; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201604199
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: A de novo synthetic method towards apiose, a structurally unusual furanose, is reported. The key feature is sequential metal catalysis consisting of the palladium‐catalyzed asymmetric intermolecular hydroalkoxylation of an alkoxyallene and subsequent ring‐closing metathesis (RCM). This strategy enabled the efficient synthesis of various apiose‐containing disaccharides and a unique convergent synthesis of trisaccharides. Abstract : Special sugars call for special measures : In a concise synthetic approach to apiose, a structurally unusual furanose, the palladium‐catalyzed asymmetric intermolecular hydroalkoxylation of an alkoxyallene was followed by ring‐closing metathesis and dihydroxylation (see scheme). This strategy enabled the efficient synthesis of various apiose‐containing disaccharides and was used in a unique convergent synthesis of trisaccharides.