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Q: Recently a new monoterpene dial, dehydroiridodial, was isolated as a pungent principle of Actinidia polygama Miq., and it was synthesized by K. Yoshihara et ai (7). On the other hand, chrysomelidial (1), the stereoisomer of dehydroiridodial, was isolated from the larval defensive secretion of a chrysomelide beetle (Plagiodera versicolora) in 1977, and it was synthesized in 1978 by J. Meinwald et al. (8). Both syntheses were non-stereospecific involving tedious separation steps. We first attempted the stereocontrolled synthesis of chrysomelidial from 4-methyltricyclo[3,3,0,0^'^]octan-3-one (2) which was prepared from diethyl 2-cyclopentene-l-ylmalonate by the general method of Doering. Methylation of diethyl 2-cyclopentene-l-ylmalonate with metyl iodide followed by hydrolysis and decarboxylation afforded 2-(2-cyclopentene-lyl)propionic acid in
A:
Progress in the Synthesis of Iridoids and Related Natural Products Sachihiko Isoe 1. 2.1 Synthesis of ChrysomelidiaI(6) (Scheme 2)