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A Short Total Synthesis of rac-Peniolactol

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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

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.

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    Authors
    1. Aamer Saeed
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    E-mail: aamersaeed@yahoo.com

    Received May 23, 2002; accepted May 30, 2002

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    Saeed, A. A Short Total Synthesis of rac-Peniolactol. Monatshefte für Chemie 134, 457–463 (2003). https://doi.org/10.1007/s00706-002-0515-6

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    • DOI: https://doi.org/10.1007/s00706-002-0515-6

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