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Total Synthesis of Pyrophen and Campyrones A-C
Keith P Reber1, Hannah E Burdge2
1Department of Chemistry, Towson University , 8000 York Road, Towson, Maryland 21252, United States.
Abstract:
The first total syntheses of the natural products pyrophen and campyrones A-C, isolated from the fungus Aspergillus niger, have been achieved in six steps starting from commercially available N-Boc amino acids. Key steps in this sequence include a vinylogous Claisen condensation to achieve fragment coupling and a dioxinone thermolysis/cyclization cascade to form the α-pyrone ring. The route described herein afforded the natural products in 15-25% overall yield, furnishing sufficient material for testing in biological assays.
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