ChemInform Abstract: Ring-Closing Metathesis in the Synthesis of Large and Medium-Sized Oxacycles. Application to the Synthesis of Polyoxygenated Macrocycles.

✍ Scribed by Mercedes Delgado; Julio D. Martin

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 34 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199944060

✦ Synopsis

Ring-Closing Metathesis in the Synthesis of Large and Medium-Sized Oxacycles. Application to the Synthesis of Polyoxygenated Macrocycles.

-A comprehensive study to the scope and limitations of ring-closing metathesis (RCM) in the cyclization of trans-substituted oxanes containing terminal double bonds at the side chains is presented. The reactions occur with great efficiency in the cyclization of oxepene and oxocene rings, but increasing ring sizes lead to decreasing yields. The introduction of an additional oxygen atom makes the RCM more effective. Several ortho-condensed oxane-polyoxygenated macrocycles (with ring sizes from 15 to 21 members) are synthesized from the corresponding dienes with excellent yields.