Premium
Synthetic Strategies for Converting Carbohydrates into Carbocycles by the Use of Olefin Metathesis
Author(s) -
Madsen Robert
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600614
Subject(s) - chemistry , olefin metathesis , ring closing metathesis , metathesis , carbene , ring (chemistry) , acyclic diene metathesis , salt metathesis reaction , ruthenium , organic chemistry , olefin fiber , total synthesis , combinatorial chemistry , stereochemistry , catalysis , polymerization , polymer
This microreview covers recent advances in the use of ring‐closing metathesis for the synthesis of carbocycles from carbohydrates. Various strategies for the synthesis of α,ω‐dienes from carbohydrates are presented, which give rise to a large variety of dienes with different stereochemistries, protecting groups and substituents. Subsequent ring‐closing metathesis with a ruthenium carbene complex affords highly functionalized carbocycles with ring sizes ranging from five‐ to eight‐membered rings. The application of these methods for the synthesis of carbocyclic natural products from carbohydrates is also demonstrated.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)