Orientalone

The ( )-benzyltetrahydroisoquinoline (149), with 3, 7- rather than 4, 7-dihydroxylation as in (142), was coupled - using potassium ferricyanide to the spiroketone (ISO), as a pair of diastereoisomers (up to 50% yield). One stereoisomer, on reduction of carbonyl and aqueous acid treatment, was converted to the new spirodienone (151), the alkaloid orientalone. 

Acetyl-2-hydroxy-8-methoxy-6-methyl-1,4-naphthoquinone, in A-10017 1 -(3,4-Dihydroxyphenyl)-1 -(2,4,6-trihydroxyphenyl)ethylene, D-20176 Orientalone, in A-10017 Pratenol A, P-20136... 

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