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(-)-Methyl Cucurbate and (-)-Methyl Jasmonate by Kinetic Resolution

✍ Scribed by Borm, Claudia ;Winterfeldt, Ekkehard

Publisher: John Wiley and Sons
Year: 2006
Tongue: English
Weight: 598 KB
Volume: 1996
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199619960722

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✦ Synopsis

Abstract

The kinetic resolution of a malonate‐substituted cyclopentenone gave rise to the formation of an enantiopure Diels‐Alder adduct which was converted into methyl dehydrocucurbate 2 by diastereoselective alkylation with (Z)‐1‐bromo‐2‐pentene and subsequent borohydride reduction. Selective hydrogenation of 2 with a palladium/calcium carbonate catalyst proved to be a reliable route to (–)‐methyl cucurbate (1) the oxidation of which with pyridinium chlorochromate and subsequent treatment with acid afforded (–)‐methyl jasmonate (9).

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