Synthesis of the Geranyl-a-pyron (⁺_-) - 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

Page (from - to)

333-335

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