Synthesis of natural product hybrids by the Ugi reaction in complex media containing plant extracts

October 17, 2022

Title

Synthesis of natural product hybrids by the Ugi reaction in complex media containing plant extracts

Author

Keisuke Tomohara, Nao Ohashi, Tatsuya Uchida & Takeru Nose

Year

2022

Journal

Scientific Reports

Abstract

Plant extracts are rich in a wide variety of molecules with diverse biological activities. Chemical engineering of plant extracts has provided a straightforward and simultaneous synthetic route for artificial molecules derived from plant products. This study achieved the synthesis of 13 natural product-like molecules by the Ugi multicomponent reaction using plant extracts as substrates. In particular, the engineering of a mixture of plant extracts demonstrated a unique synthetic route to a series of natural product hybrids, whereby otherwise unencountered naturally occurring molecules of different origins were chemically hybridized in complex media. Even though these reactions took place in complex media containing plant extracts, the well-designed process achieved a good conversion efficiency (~ 60%), chemoselectivity, and reproducibility. Additionally, some of the Ugi adducts exhibited promising inhibitory activity toward protease.

Instrument

FT/IR-4700, FP-8500, V-660

Keywords

biological activities, natural product, chemoselectivity