What question did this study set out to answer?

The aim is to achieve the total synthesis of specific spermidine alkaloids using accessible starting materials.

May 15, 2026ChemistrySelect0 citations

First Total Synthesis of N 1 ‐Dihydrocaffeoyl ‐ N 10 ‐Caffeoyl Spermidine and (±) ‐ Lycium Spermidine A

LHLili HeNingxia Academy of Agriculture and Forestry Sciences LZLijuan ZhaiNingxia Academy of Agriculture and Forestry Sciences JJJingwen JiNingxia Academy of Agriculture and Forestry Sciences

Key Points

The aim is to achieve the total synthesis of specific spermidine alkaloids using accessible starting materials.
First total synthesis of N1-dihydrocaffeoyl-N10-caffeoyl spermidine and (±)-Lycium spermidine A.
Processes include six and seven synthetic steps leading to commercially acceptable yields.
A crucial step involves reducing a nitrile to an amine and forming an amide bond in one pot.
Successfully synthesized both spermidine alkaloids with high efficiency.
Yielded commercially acceptable amounts that could support potential industrial applications.

Abstract

ABSTRACT Spermidine alkaloids are naturally occurring polyamines widely found in medicinal plants of the Solanaceae family. They have been extensively studied for their neuroprotective and anti‐inflammatory properties. Herein, we report the first total synthesis of N 1 ‐dihydrocaffeoyl‐ N 10 ‐caffeoyl spermidine and (±)‐Lycium spermidine A using readily available starting materials. The synthetic routes allow efficient preparation in commercially acceptable yields over six and seven steps. A key synthetic step involves reducing a nitrile to an amine and simultaneously reacting it with an activated acid to form an amide bond in one pot. This synthetic approach may facilitate the production of these compounds on an industrial scale.

Ask AI

Helpful

Bookmark

View Full Paper