Cviii. Studies in the Biochemistry of Micro-organisms Lviii. Synthesis of Spinulosin (3:6-dihydroxy-4- Methoxy-2:5-toluquinone) a Metabolic Product of Penicillium

Studies in the Biochemistry of Micro-Organisms

Bracken, Pocker & Raistrick (1954) described the isolation of two nitrogen-containing products from different cultures of Penicillium cyclopium Westling. One of these, previously isolated from Penicillium viridicatum Westling by Cunningham & Freeman (1953) and named viridicatin, C15H11NO2, was shown to be 2,3-dihydroxy-4phenylquinoline or its keto-tautomer (I), by degradative methods and unequi...

Studies in the biochemistry of micro-organisms: 72. Gentisyl alcohol (2:5-dihydroxybenzyl alcohol), a metabolic product of Penicillium patulum Bainier.

Studies in the biochemistry of micro-organisms: Synthesis of cynodontin (1:4:5:8-tetrahydroxy-2-methylanthraquinone), a metabolic product of species of Helminthosporium.

SYNTHESIS OF (k) - 6,8-DIHYDROXY-3- ISOPROPYL-7-METHYLISOCHROMAN

The title isochroman ( 8 ) was synthesized as a suitable substrate for acetoxylation studies leading to an intermediate of type (4), expected to afford, on condensation with diketen, the fungal metabolite "rotiorin" type linear product (1). Cyclocondensation of alcohol (6), obtained by the reduction of ketone (5) with paraform in the presence of anhydrous aluminum chloride afforded the dim...

" BISCYCLISATION" SYNTHESIS OF 1,8-DIHYDROXY-9, 1 0- ANTHRAQUINONE (1,8-DHA)

The synthetic route in this work is based on the classical Friedel-Crafts strategy, and began with 1,4-dimethoxybenzene (I), followed by alkylation and selective demethylation of 2-methoxy function in 0x0-acid (3). The orthoformylation to synthesize aldehyde (6) was based on the Reimer-Tieman reaction. Chain extension of this aldehyde required methylation of the hydroxyl group and condensat...