Synthesis of Murisolin, (15<i>R</i>, 16<i>R</i>, 19<i>R</i>, 20<i>S</i>)‐Murisolin A, and (15<i>R</i>, 16<i>R</i>, 19<i>S</i>, 20<i>S</i>)‐16,19‐<i>cis</i>‐Murisolin and Their Inhibitory Action with Bovine Heart Mitochondrial Complex I

Abstract

The asymmetric total synthesis of murisolin, (15R, 16R, 19R, 20S)-murisolin A, and (15R, 16R, 19S, 20S)-16,19-cis-murisolin was performed by using an epoxy alcohol as a versatile chiral building block for synthesizing the stereoisomers of mono-THF annonaceous acetogenins. The inhibitory activity of these murisolin compounds was examined with bovine heart mitochondrial complex I, and they showed almost the same activity.