Synthetic transformations of sesquiterpene lactones 9.* Synthesis of 13-(pyridinyl)eudesmanolides

• DOI: 10.1007/s10593-016-1855-1
• Publication Date: 2016-04-27T00:53:20Z
• Authors: Sergey S. Patrushev; Makhmut M. Shakirov; Elvira E. Shults
• Keywords: Furan; Sesquiterpene lactone

The reaction of isoalantolactone, a sesquiterpene α-methylidene-γ-lactone, with bromo(iodo)pyridines under the Heck reaction conditions gave 3-(pyridylmethylidene)-8а-methyldecahydronaphtho[2,3-b]furan-2(3Н)-ones and 3-(pyridylmethyl)-8а-methyloctahydronaphtho[2,3-b]-furan-2(4Н)-ones, products of double bond migration. The yield and product ratio depended on the reaction conditions and the nature of halopyridine. The effectiveness of Pd(OAc)2–caffeine catalytic system was demonstrated in this reaction.