✍ Scribed by Aamer Saeed
No coin nor oath required. For personal study only.
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.
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## Abstract A simple route to 3‐(hydroxymethyl‐^14^C)‐8‐methoxychromone‐2‐^14^ using formaldehyde‐^14^C is described. However, this material was considered to be unacceptable for most biological studies because about 16% of the radioactivity was expired as ^14^CO~2~ in the mouse. The synthesis of 3