Title

De Novo Synthesis of Furanose Sugars: Catalytic Asymmetric Synthesis of Apiose and Apiose-Containing Oligosaccharides.

Authors

Kim, Mijin; Kang, Soyeong; Rhee, Young Ho

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.

Subjects

SUGAR synthesis; FURANOSIDES; OLIGOSACCHARIDE synthesis; ASYMMETRIC synthesis; TRISACCHARIDES; DISACCHARIDES; CATALYSIS

Publication

Angewandte Chemie, 2016, Vol 128, Issue 33, p9885

ISSN

0044-8249

Publication type

Academic Journal

DOI

10.1002/ange.201604199