Studies in the biochemistry of micro-organisms. 105. Chemical degradation of sclerotiorin

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Abstract
The product of the reaction of sclerotiorin obtained from Penicillium multicolor with ammonia, C21H24O4NCl, named sclerotiorazin, is readily reduced by zinc and acetic acid, yielding sclerotazin (C19H22O2NCI) and acetic acid. By mild alkaline hydrolysis of sclerotazin the chlorine atom is eliminated and replaced by a hydroxyl group, affording hydroxydechlorosclerotazin, C19H23O3N. Sclerotazin forms a diacetate, from which the unsaturated side chain is removed by ozonolysis and replaced by a carboxyl group, affording the diacetate of sclerazinic acid C11H8O4NCl. Oxidation of sclerazinic acid with alkaline potassium permanganate solution gives berberonic acid. From these degradations a tentative partial molecular structure for sclerotazin is deduced. Sclerotiorin reacting with methylamine produces N-methylsclerotiorazin (C22H26O4NCl), which is reduced by zinc and acetic acid to deacetyldihydro-N-methylsclerotio-razin, C20H26O3NCl.