Facile synthesis of the fungus-derived natural products: N,N'-dipalmitoleyl urea (C 16:1) and N,N'-dioleyl urea (C 18:1)

Nat Prod Res. 2020 Nov 12;1-8. doi: 10.1080/14786419.2020.1844694. Online ahead of print.

Abstract

Oxalyl chloride is one of the most versatile reagents used in organic synthesis. Oxalyl chloride was employed in the convenient one-pot, two-step synthesis of the fungus-derived naturally occurring lipoids: N,N'-dipalmitoleyl urea (C16:1) and N,N'-dioleyl urea (C18:1). The two symmetrical diacyl urea-based natural products were previously identified as fungus-specific pathogen-associated molecules (PAMs), which act as inflammatory mediators during fungal infection. The highly lipophilic natural lipoids were efficiently synthesized from commercially available reagents in yields ranging from good to very good.

Keywords: Oxalyl chloride; diacyl urea (DAU); fungal natural products; lipoid; one-pot reaction; pathogen-associated molecules (PAMs).