Semi-syntheses and interrogation of indole-substituted Aspidosperma terpenoid alkaloids

Abstract

We demonstrated here a series of Aspidosperma terpenoid alkaloids can be quickly prepared using semisynthesis from naturally sourced tabersonine, featuring multiple oxygen-based substituents on the indole ring such as hydroxy...

Inhibition of mitochondrial metabolism by (−)-jerantinine A: synthesis and biological studies in triple-negative breast cancer cells

“…One of our laboratories (Moses et al ) developed a sustainable semi-synthesis of (−)- JA from the indole alkaloid (−)-tabersonine ( TAB , 3 ) in nine synthetic steps and an overall yield of 29%. 12 Wang et al recently developed a site-selective enzymatic oxidation of TAB , 16 that enabled access to JA in up to 25% overall yield. We now report an improved four-step, protecting group-free semi-synthesis of (−)- JA in 51% overall yield.…”