Mollisin, a naturally occurring chlorine‐containing quinone: Part III,. The synthesis of dechloromollisin methyl ether and of related compounds

Abstract

A survey is given of the synthetic experiments which have led finally to the synthesis of 8-acetyl-5-methoxy-2,7-dimethylnaphthoquinone-l,4. The synthetic compound proved to be identical with dechloromollisin methyl ether.Additional evidence is presented for the structure of the compound, Iertcoanhydrodechloromollisin.In the preceding paper 1 the following structure was derived for mollisin, the yellow chlorine-containing pigment produced by the fungus Mollisiu vaesiu :This paper presents synthetic evidence for the correctness of this structure. The synthesis and the oxidation of 4acetyl-1-methoxy-3-methylnaphthalene; a new method of preparing a-naphthoquinonesSeveral naphthalene derivatives can be oxidized directly to the corresponding a-naphthoquinones by chromium trioxide in acetic acid; e.g., from 1-benzoylnaphthalene, 5-benzoylnaphthoquinone-

Unexpected Formation of a 1,2-Dichloroacenaphthylene in a Friedel-Crafts Reaction with Chloral Hydrate

“…The reaction of 1,8-dimethoxy-3,6-dimethylnaphthalene [5] (1) with chloral hydrate in the presence of concentrated sulfuric acid leads to the formation of 1,2-dichloro-5,6-dimethoxy-3,8-dimethylacenaphthylene (2) in 41 % yield (Scheme 1).…”