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An enantioselective total synthesis of novel gingerol-related compound 4-((3 S ,5 R )-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.

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