Syntheses and Potato Tuber-inducing Activities of Unnatural Long-chain OPC-9:0 and OPC-10:0

Abstract

  The unnatural long-chain OPCs, OPC-9:0 and OPC-10:0, were respectively synthesized from the ethyl esters of OPC-7:0 and OPC-8:0. C₂-carbon elongation was achieved via alkylation of the enolate of tert-butyl acetate. The potato tuber-inducing activity of OPC-10:0, as well as OPC-8:0, -6:0 and -4:0, was similar to that of jasmonic acid. OPC-9:0 also exhibited weak tuber-inducing activity.