Total synthesis of 4-((3S,5R)-3,5-dihydroxynonadecyl)phenol

Abstract

An enantioselective total synthesis of novel gingerol-related compound 4-((3S,5R)-3,5-dihydroxynonadecyl)phenol, an anti-oxidant isolated from the resinous exudates of Chilean desert plants, has been accomplished from a known commercially available 4-(but-3-enyl) phenol by a concise ten-step sequence. In this synthesis, Sharpless asymmetric dihydroxylation, Grignard reaction and Iodine-induced electrophilic cyclization have been applied as key steps.

Graphical Abstract

Keywords:

• (3,5-Dihydroxynonadecyl) phenol
• Grignard reaction
• iodolactonization
• regioselective ring opening
• sharpless asymmetric dihydroxylation

Acknowledgments

The authors are thankful to Chemistry Division, Department of Sciences and Humanities, Vignan Foundation for Science Technology and Research, Guntur for constant encouragement in providing laboratory facilities and analytical data.