One-Flask Tethered Ring Closing Metathesis–Electrocyclic Ring Opening for the Highly Stereoselective Synthesis of Conjugated Z/E-Dienes

✍ Scribed by Bernd Schmidt; Oliver Kunz

• Book ID: 102830122
• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 816 KB
• Volume: 2012
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.201101497

✦ Synopsis

Abstract

A one‐flask reaction sequence comprising ring closing metathesis (RCM) of butenoates derived from allylic alcohols and a base‐mediated ring opening gives 2__Z__,4__E__‐configured dienoic acids in high yields and stereoselectivities. Application of the method to the synthesis of the natural product fusanolide A suggests that the originally published structure was erroneously assigned and should be revised.