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Paper | Regular issue | Vol 31, No. 8, 1990, pp.1485-1490
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5423
Synthesis of Nectriafurone, an Isofuranonaphthoquinone Isolated from the Fungus Nectria haematococca

Michel Devys, Michel Barbier,* and Denise Parisot

*Institut des Chimie des Substances Naturelles, C.N.R.S., 1 avenue de la Terrasse, Bat. 27, 91198 Gif-sur-Yvette Cedex, France

Abstract

Synthesis of 5-methoxy-4,7-dihydroxynaphtho[2,3-c]8,9-furandione (2) and of 4,7-dihydroxynaphtho[2,3-c]8,9-furandione (3) were carried out by a rapid Friedel-Crafts reaction using the dry method. The addition of acetaldehyde on 2 in presence fo LDA gave the (±)-nectriafurone (1), thus cofirming the proposed structure of 3-(1‘-hydroxyethyl)-5-methoxy-4,7-dihydroxynaphtho[2,3-c]8,9-furandione.