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

Publikations-Art

Zeitschriftenbeitrag (peer-reviewed)

Autoren

Schmidt, D.; Conrad, J.; Klaiber, I.; Mika, S.; Beifuss, U.

Erscheinungsjahr

2007

Veröffentlicht in

Synlett

Band/Volume

nnb/2

Seite (von - bis)

333-335

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.