Quan Zhou1, Barry B Snider. 1. Department of Chemistry, MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Abstract
A practical route to the labile tetracyclic isoxazolo[4,3,2-de]phenanthridinone moiety of the antifungal parnafungins has been developed. Zinc reduction of a methyl 2'-hydroxymethyl-2-nitro-3-biphenylcarboxylate, which was prepared by a Suzuki coupling, afforded a benzisoxazolone that was treated with MsCl and base to generate the labile tetracyclic ring system in 37-47% yield. This compound decomposes to the phenanthridine in CDCl(3) and the phenanthridine N-oxide in aqueous base.
A practical route to the labile tetracyclic isoxazolo[4,3,2-de]phenanthridinone moiety of the antifungal n class="Chemical">parnafungins has been developed. Zinc reduction of a methyl 2'-hydroxymethyl-2-nitro-3-biphenylcarboxylate, which was prepared by a Suzuki coupling, afforded a benzisoxazolone that was treated with MsCl and base to generate the labile tetracyclic ring system in 37-47% yield. This compound decomposes to the phenanthridine in CDCl(3) and the phenanthridine N-oxide in aqueous base.
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