A Concise Synthesis of Pawhuskin A

• Published in: Journal of natural products (Washington, D.C.) Vol. 71; no. 11; pp. 1949 - 1952
• Main Authors: Neighbors, Jeffrey D, Buller, Matthew J, Boss, Kelly D, Wiemer, David F
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society and American Society of Pharmacognosy 01.11.2008; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: Chemistry; Chemistry, Medicinal; Exact sciences and technology; Fabaceae - chemistry; Life Sciences & Biomedicine; Molecular Structure; Noncondensed benzenic compounds; Organic chemistry; Pharmacology & Pharmacy; Plant Sciences; Preparations and properties; Science & Technology; Stereoisomerism; Stilbenes - chemical synthesis; Stilbenes - chemistry; Terpenes - chemical synthesis; Terpenes - chemistry; MACARANGA-SCHWEINFURTHII; STILBENES; METALATION; ANALOGS; SALVINORIN; Aldehydophenols; Horner Emmons reaction; Isoprenoid; Chemical synthesis; Stilbene derivatives
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np800351c

Pawhuskin A is an isoprenylated stilbene that was isolated from Dalea purpurea and reported to have affinity for the opioid receptor in vitro. It has been synthesized through a convergent sequence that joins a prenylated aldehyde with a geranylated phosphonate in a stereoselective Horner−Wadsworth−Emmons condensation to afford the target E olefin isomer. This synthesis confirms the structure assigned to the natural product and establishes a route that may be used to explore its biological activity and to prepare more active analogues.