Asymmetric Total Synthesis of Eupalinilide E, a Promoter of Human HSPC Expansion

ABSTRACT: A concise and scalable asymmetric total synthesis of eupalinilde E from (R)-(???)-carvone in 12 steps is reported with an overall yield of 20%. The key steps of the synthesis are a tandem Favorskii rearrangement???elimination reaction in the chromatography-free synthesis of carvone-derived 2-cyclopentene carbaldehyde and its catalyst-free stereospecific tandem allylboration???lactonization using recyclable trifluoroethanol as a promoter and solvent affording ??-hydroxymethyl-??methylene-??-butyrolactone.

Automated summary

A concise and scalable asymmetric total synthesis of eupalinilde E, starting from (R)-(???)-carvone, is reported in this article. The synthesis involves 12 steps and achieves an overall yield of 20%. Key steps include a tandem Favorskii rearrangement???elimination reaction for the chromatography-free synthesis of carvone-derived 2-cyclopentene carbaldehyde, and a catalyst-free stereospecific tandem allylboration???lactonization using recyclable trifluoroethanol as a promoter and solvent, leading to the formation of ??-hydroxymethyl-??methylene-??-butyrolactone.