The synthesis of the pyranonaphthoquinones dehydroherbarin and anhydrofusarubin using Wacker oxidation methodology as a key step and other unexpected …

A Pillay, AL Rousseau, MA Fernandes…

Index: Pillay, Adushan; Rousseau, Amanda L.; Fernandes, Manuel A.; De Koning, Charles B. Organic and Biomolecular Chemistry, 2012 , vol. 10, # 38 p. 7809 - 7819

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Citation Number: 5

Abstract

The synthesis of two closely related pyranonaphthoquinones, dehydroherbarin and anhydrofusarubin, is described. The construction of the naphthalene nuclei was achieved using the Stobbe condensation reaction using 2, 4-dimethoxybenzaldehyde and 2, 4, 5- trimethoxybenzaldehyde as their respective starting materials. Two key steps en route include a PIFA-mediated addition of a methoxy substituent onto the naphthalene skeleton ...