A short synthesis of the anti-leukemic sesquiterpene (+)-caparratriene employing aqueous Wittig chemistry

✍ Scribed by Priyabrata Das; James McNulty

• Book ID: 104097722
• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 237 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2010.04.035

✦ Synopsis

An efficient, stereoselective method for the synthesis of (+)-caparratriene based on an aqueous Wittig reaction has been developed. A functionalized triethylallyl ylide reacted under various conditions with (+)-citronellal to deliver (+)-caparratriene in only three steps with excellent overall yield. The Wittig reaction proceeded with exclusive (4E)-selectivity and an interesting cationic effect was uncovered with good stereoselectivity at the isomerizable allylic position being observed in the presence of lithium salts.