Concise Synthesis of Pentenyl Phenyl Acrylic Acid

Abstract

Pentenyl phenyl acrylic acid is a structural unit of pepticinnamin E, a natural product and a bisubstrate inhibitor of FPTase. In this article, a new synthetic strategy was developed to prepare pentenyl phenyl acrylic acid with high stereoselectivity and high overall yield of 78.6%. The method used in producing these effects involved the application of a five‐step procedure. Pentenyl phenyl acrylic acid was synthesized starting from 2‐iodo‐benzyl alcohol through an E‐selective Wittig–Horner reaction, and then the Sonogashira reaction was used to produce 2‐(1‐pentynyl)‐E‐ethyl‐cinnamoylate, which was quantitatively hydrogenated, catalyzed by Lindlar catalyst.

Keywords:

• pentenyl phenyl acrylic acid
• quantitative hydrogenation
• Sonogashira reaction
• stereoselectivity
• Wittig–Horner reaction

Acknowledgment

The authors thank the Chengdu Institute of Organic Chemistry, CAS, and Shandong University at Weihai for financial support.