The Journal of Organic Chemistry

Regiocontrolled synthesis of hydroxyphthalides. Synthesis of (.+-.)-isoochracinic acid and a zealeranone intermediate

BM Trost, GT Rivers, JM Gold

文献索引：Trost, Barry M.; Rivers, Gordon T.; Gold, Jeffrey M. Journal of Organic Chemistry, 1980 , vol. 45, # 10 p. 1835 - 1838

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被引用次数: 58

摘要

Metalation of 3-methoxy-and 3, 5-dimethoxybenzyl alcohol followed by quenching with COz provided the phthalides. Bromination and solvolysis generated 7-methoxy-and 5, 7- dimethoxyphthalaldehydic acid in a fully regiocontrolled reaction. The former served as an intermediate in the synthesis of isoochracinic acid, a toxic metabolite from a parasite responsible for black spot disease of Japanese pears, in 44% overall yield from 3- ...