Total synthesis of 3,7-dimethyl-7-hydroxy-2-octen-1,6-olide and 3,7-dimethyl-2,6-octadien-1,6-olide

Abstract

3,7-Dimethyl-7-hydroxy-2-octen-1,6-olide (1) and 3,7-dimethyl-2,6-octadien-1,6-olide (2), the natural bioactive compounds isolated from the fruit of Litsea cubeba and the liverwort Plagiochila rutilans, were totally synthesized using easily available cis-geraniol as raw material in short, convenient, and low-cost, five-step reactions including three steps of oxidation, cyclization, and dehydration, with an overall yield of 47.5% and 37.3%.

Keywords:

• total synthesis
• 3,7-dimethyl-7-hydroxy-2-octen-1,6-olide
• 6-olide
• 3,7-dimethyl-2,6-octadien-1,6-olide

Acknowledgments

This study was co-founded by Natural Science Foundation of China (No. 21172254), the National Key Technologies R&D Program (No. 2011BAE06B04), National Hi-Tech R&D Program of China (2011AA10A202), and Chinese Universities Scientific Fund (2012YJ131).