6533b820fe1ef96bd127a352

RESEARCH PRODUCT

ChemInform Abstract: Ring-Opening Aminolysis of Sesquiterpene Lactones: An Easy Entry to Bioactive Sesquiterpene Derivatives. Synthesis of (+)-β-Cyperone and (-)-Eudesma-3,5-diene from Santonin.

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Abstract Santonin ( 1 ) and other sesquiterpene lactones ( 2–3 ) react with pyrrolidine and other cyclic secondary amines to afford γ-hydroxyamides, which by elimination with mesyl chloride in pyridine-benzene at 80°C give unsaturated amides 4a-4c, 5a-5c and 6 . Starting from amides 5a-5c a series of bioactive compounds against Locusta migratoria have been prepared, differing in the oxidation states of the C-3 and C-12 carbon atoms. Starting from amides 5a and 6 two conjugated diene eudesmanes (+)-β-cyperone ( 15 ) and (−)eudesma-3,5-diene ( 19 ) have been prepared involving an elaboration of the amide group of the side chain of the eudesmane skeleton.