Syntheses of methyl dl-jasmonate (1) and methyl dl-2-epijasmonate (2) from 3a,7a-cis-3a,4,7,7a-tetrahydro-lindanone (3a) are described. Efficient construction of the carbomethoxymethyl and cis-pentenyl moieties could be achieved by developing a successful method for a key step, the partial oxidation of aldehyde hemiacetal 6, prepared from 3a, to acid hemiacetal 7a. The methyl ester of 7a was converted to both 1 and 2 by different routes via the thioacetals 8b and 11, respectively.
ASJC Scopus subject areas
- Organic Chemistry