First consecutive linear synthesis of hostmaniene, 5-formyl-2-(isopropyl-1’-ol)benzofuran and anadendroic acid using prenylated phenol

Mohd Fazli Mohammat , Nur Shazwani Osman, Zurina Shaameri and Ahmad Sazali Hamzah

Organic Chemistry Laboratory, Institute of Science, Universiti Teknologi MARA, Kampus Puncak Alam, 42300 Bandar Puncak Alam, Selangor, Malaysia

Department of Chemistry, Faculty of Applied Sciences, Universiti Teknologi MARA, UiTM Shah Alam,40450 Shah Alam, Selangor, Malaysia

Abstract: The paper describes a new pathway for the syntheses of three natural bioactive benzofuran type compounds, namely, hostmaniene, 5-formyl-2-(isopropyl-1’-ol)benzofuran and anadendroic acid. The key synthetic strategy involved prenylation of the carboxy-phenol 7 and followed by the [5-exo-tet]cyclization reaction to furnish the benzofuran ring synthon. Subsequently, performing sequences of reactions of epoxide ring opening, ester reduction and re-oxidation of the alcohol from the benzofuran ring synthon gave all the title compounds in reasonable yield. Their structures were confirmed by both spectroscopic data and chemical transformations.  

Keywords: Hostmaniene ; anadendroic acid ; prenylated pheno ; benzofuran . © 201 7 ACG Publications. All rights reserved.