A Convenient Synthesis of (-)-Methyl Epijasmonate

Abstract

A short, enantioselective synthesis of (-)-methyl epi-jasmonate, ent-1, has been achieved starting from readily available Corey lactone aldehyde 9. The key features include the stereoselective installation of 2,3-cis-disubstituted side-chains by hydrogenation of dienoate 8 and subsequent one-carbon degradation.

Notes

Moreover, the preparation of the unnatural jasmonoid (-)-1 would be useful in clarifying conflicting reports on an interesting structure-activity relationship: see ref 2c and references cited therein.

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