Total synthesis of (±)-spirotenuipesine A, a promoter of neurotrophic factor secretion from glial cells

Abstract

Naturally occurring (+)-spirotenuipesines A and B are known to promote the biosynthesis of neurotrophic factors in glial cells. Therefore, these compounds can be expected to constitute promising drug leads for neurodegenerative diseases such as Alzheimer's disease. In order to obtain sufficient amounts for biological evaluation, (±)-spirotenuipesine A was synthesized via a stereoselective Ireland-Claisen rearrangement as a key step. A culture medium of 1321N1 cells treated with the obtained synthetic racemic compound showed differentiation-inducing activity against PC12 cells, resulting in a morphological change.