65391-44-8Relevant articles and documents
Synthesis of a ring-oxygenated variant of the 2-carboxy-6- hydroxyoctahydroindole core of aeruginosin 298-A from glucose
Nie, Xiaoping,Wang, Guijun
, p. 8687 - 8692 (2007/10/03)
The design and synthesis of a new core structure, a ring-oxygenated variant of 2-carboxy-6-hydroxyoctahydroindole (Choi) from D-glucose, is reported. Choi, a rigid bicyclic unnatural amino acid, is the core structure of about 15 aeruginosins natural compounds. These compounds are thrombin, trypsin, and factor VIIa inhibitors and Choi is important for their biological activity. The ring-oxygenated variant of 2-carboxy-6-hydroxyoctahydroindole can potentially be used as a surrogate of Choi in the design and synthesis of aeruginosin-based thrombin inhibitors. & 2005 American Chemical Society.
Out-of-Ring Claisen Rearrangement are Highly Stereoselective in Pyranoses: Routes to gem-Dialkylated Sugars
Tulshian, Deen Bandhu,Tsang, Raymond,Fraser-Reid, Bert
, p. 2347 - 2355 (2007/10/02)
The Claisen rearrangement has been evaluated as a means for stereoselective creation of functionalized geminal substituents at C-2 and C-3 of hexopyrano systems.C-2 and C-3 keto sugars react with Wittig reagents to give α,β-unsaturated esters, one geometric isomer being obtained in each case.Reduction of the ester and trans vinylation with ethyl vinyl ether leads to allyl vinyl ethers wich are thermolysed in refluxing benzonitrile.The oxy-Cope rearrengement proceeds with complete stereoselectivity, the folding pattern being always from the β-face of the pyranose ring.Thus, the acetaldehyde moiety ends up axially oriented at C-2 and equatorially oriented at C-3.These stereochemical results are not affected by neighboring oxygen substituents nor by the presence or absence of an anomeric alkoxyl functionality.