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between anhydrofusarubin lactol and ammoniawas shown on an other side to be responsible for the formation of the antibiotic bostrycoidin2). This 2-aza-anthraquinone was accompanied by a 6-0demethyl-5-deoxy derivative in a selected mutant of N. haematococca^. The structural variations observed in the various naphthopyranones result from subsequent methylations or hydroxylations of the original heptaketide40. In order to study such biogenetic correlations, mutants of Nectria haematococca blocked at different points of their pigment production were selected5). These mutants are all mappedin a single chromosomalregion consisting of at least three genes6) responsible for the transformations of the heptaketide. It has been possible to establish that two of these genes (YEL Y and YEL J) were controlling respectively O-methylations and hydroxylations of the cyclized heptaketide-derived precursor1 ~ 3> 5 ~ 8). in this context, the 4-deoxyfusarubin (1) and the corresponding anhydro compound 2 were previously isolated40 from Nectria haematococca. (The classical numbering system for the naphthopyranone structure has been adopted here, as shownon the scheme; previous publications used a different system, more adapted to biosynthetic studies and starting from the methyl group of the last acetate unit). As the selected 1799

A new deoxyfusarubin produced by the fungus Nectria haematococca. Synthesis of the two isomeric deoxyanhydronaphthopyranones from toralactone.