Preparation of the geranyl-α -pyrone ( )-aurantiacone via a new pyrone synthesis

Publication Type
Journal contribution (peer reviewed)
Authors
Schmidt, D.; Conrad, J.; Klaiber, I.; Mika, S.; Beifuss, U.
Year of publication
2007
Published in
Synlett
Band/Volume
nnb/2
Page (from - to)
333-335
Abstract

The structure of the leaf resin geranyl-α-pyrone aurantiacone isolated from Mimulus (= Diplacus) aurantiacus (Curtis) Jeps. (Scrophulariaceae) was confirmed through synthesis of (±)-aurantiacone (I). The key step is lactonization of the sensitive 5-hydroxy-3-oxopent-4-enoic acid under mild conditions, which can be released from the corresponding bispotassium salt. The latter was accessible in a few steps from an N-acyl aziridine and an Et acetoacetate.

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