A Short Total Synthesis of <Emphasis Type="Italic">rac</Emphasis>-Peniolactol

Summary.  A short facile synthesis of the fungal metabolite (±)-3,4-dihydro-3,6,8-trihydroxy-3- pentadecylisocoumarin (peniolactol) has been achieved. Condensation of hexadecanoyl chloride with 3,5-dimethoxyhomophthalic acid afforded 6,8-dimethoxy-3-pentadecylisocoumarin, which on sequential saponification and demethylation furnished rac-peniolactol in 31% overall yield. The ring-chain tautomerism was studied in solution by ¹H NMR and the mass fragmentation pattern. 3-Pentadecyl- isocoumarin was also synthesized and saponified to the corresponding keto acid as a model compound for comparative studies. E-mail: aamersaeed@yahoo.com Received May 23, 2002; accepted May 30, 2002