Syntheses of methyl dl-jasmonate and methyl dl-2-epijasmonate

Hideo Tanaka, Sigeru Torii

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Abstract

Syntheses of methyl dl-jasmonate (1) and methyl dl-2-epijasmonate (2) from 3a,7a-cis-3a,4,7,7a-tetrahydro-1-indanone (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.

Original languageEnglish
Pages (from-to)462-465
Number of pages4
JournalJournal of Organic Chemistry
Volume40
Issue number4
Publication statusPublished - 1975

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ASJC Scopus subject areas

  • Organic Chemistry

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