Highly Functionalised Cyclobutanols by Samarium(II) Iodide Induced Radical Cyclisations of Carbohydrate-Derived Unsaturated Ketones

✍ Scribed by D. Bradley G. Williams; Kevin Blann

• Publisher: John Wiley and Sons
• Year: 2004
• Tongue: English
• Weight: 127 KB
• Volume: 2004
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200400220

✦ Synopsis

Abstract

Certain carbohydrates have been found to be excellent precursors for the samarium diiodide‐mediated 4‐exo‐trig cyclisation reaction of their keto‐olefin derivatives, which were readily prepared in a few easy steps. The cyclisation was found to be stereoselective, affording cis products, the diastereoselective excesses of which were influenced by the nature of the protecting group employed at C5−O of the furanose sugar. The major chiral cyclobutane product of the cyclisation step was converted into an advanced intermediate for the synthesis of a nucleoside anti‐viral analogue. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)