European Journal of Organic Chemistry

Synthesis of (±)??Methyl Epijasmonate and (±)??Methyl Dihydroepijasmonate by Diastereoselective Protonation

N Krause, S Ebert

文献索引：Krause, Norbert; Ebert, Sophia European Journal of Organic Chemistry, 2001 , # 20 p. 3837 - 3841

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被引用次数: 11

摘要

Abstract The synthesis of (±)-methyl epijasmonate (1) was carried out by Michael addition of lithium diallylcuprate to enone 3 and diastereoselective enolate protonation with the chelating proton source 2-(methyliminomethyl) phenol (4; 85% ds), followed by ozonolysis, oxidation, esterification, and Lindlar hydrogenation. During the ozonisation, epimerization to the thermodynamically more stable trans-isomer takes place to some extent, so that 1 was ...