First Synthesis of the Naturally Occurring Diazocarbonyl Compound Cremeomycin

Abstract

The first synthesis of cremeomycin (3-diazo-4-methoxy-2-oxocyclohexa-4,6-dienecarboxylic acid), a naturally occurring diazocarbonyl compound, is described. Starting from methyl 2-hydroxy-4-methoxybenzoate, nitration, hydrolysis, and reduction gave 3-amino-2-hydroxy-4-methoxybenzoic acid as the key aminophenol precursor, diazotization of which gave the diazoquinone natural product.

Key words

natural products - total synthesis - diazo compounds - electrophilic aromatic substitution

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