Synthesis of a Common Cyclopentanoid Building Block for the Total Synthesis of Jatropha-5,12- and -6(17),11-dienes by Uncatalyzed Intramolecular Carbonyl­ Ene (ICE) Reaction

Abstract

We report the scalable synthesis of a common cyclopentanoid building block for 15-hydroxyjatropha-5,12- and -6(17),11-dienes in 11 steps. Key to the synthesis is an uncatalyzed intramolecular carbonyl ene (ICE) reaction of an ε,ζ-unsaturated α-keto ester.

Key words

terpenoids - total synthesis - ene reaction - substituent effects - pericyclic reaction

• References


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