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De Novo Synthesis of Furanose Sugars: Catalytic Asymmetric Synthesis of Apiose and Apiose‐Containing Oligosaccharides
Author(s) -
Kim Mijin,
Kang Soyeong,
Rhee Young Ho
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201604199
Subject(s) - furanose , chemistry , convergent synthesis , catalysis , metathesis , stereochemistry , ring closing metathesis , ring (chemistry) , organic chemistry , polymerization , polymer
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.