Premium
A facile synthesis of cytogenin (8‐hydroxy‐3‐hydroxymethyl‐6‐methoxyisocoumarin)
Author(s) -
Saeed Aamer
Publication year - 2004
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570410619
Subject(s) - chemistry , hydroxymethyl , regioselectivity , chloroacetyl chloride , demethylation , isocoumarin , metabolite , hydrolysis , sodium hydroxide , aqueous solution , chloride , organic chemistry , stereochemistry , catalysis , biochemistry , gene expression , dna methylation , gene
A facile and straightforward synthesis of cytogenin 1 (8‐hydroxy‐3‐hydroxymethyl‐6‐methoxyisocoumarin) metabolite of Streptoverticillium eurocidicum and Certocystis fimbriata has been achieved. Condensation of chloroacetyl chloride with 3,5‐dimethoxyhomophthalic acid 2 directly furnished 3‐chloromethyl‐6,8‐dimethoxyisocoumarin 3 which was hydrolyzed to 6,8‐dimethoxy‐3‐hydroxymethylisocoumarin 4 using 0.05% aqueous sodium hydroxide in THF. Regioselective demethylation of 4 yielded cytogenin 1 . In model experiments, 3‐chloromethylisocoumarin was prepared and converted into 3‐hydroxymethyl isocoumarin.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom