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TY - JOUR AU - Mgina, Clarence A. AU - Kadir, Fatma PY - 2018/07/31 Y2 - 2025/07/26 TI - Semisynthesis of a mellein-type 3,4-dihydroisocoumarin from cashew nut shell liquid (CNSL) JF - Tanzania Journal of Science JA - Tanz. J. Sci. VL - 44 IS - 2 SE - Articles DO - UR - http://www.tjs.udsm.ac.tz/index.php/tjs/article/view/306 SP - 128-140 AB - <p><em>Mellein-type 3,4-dihydroisocoumarin <strong>39</strong> (i.e., 8-methoxy-3-tridecyl-3,4-dihydroisocoumarin or 8-methoxy-3-tridecylisochroman-1-one), and its precursors, namely, methyl 2-methoxy-6-pentadecylbenzoate (<strong>37</strong>), methyl 2-methoxy-6-pentadecanoylbenzoate (<strong>38</strong>) and (E)-methyl 2-methoxy-6-(pentadec-1-enyl)benzoate (<strong>19</strong>) were synthesized from anacardic acid (<strong>12</strong>) as a starting material obtained from Cashew Nut Shell Liquid (CNSL) in an overall yield of 78%. The transformation of <strong>12</strong> to <strong>39</strong> involved protection of the reactive phenolic and carboxylic acid groups of compound <strong>12</strong> through methylation followed by hydrogenation so as to saturate the mono-, di- and tri-unsaturated C₁₅ chains of anacardic acid (<strong>12</strong>). Subsequent benzylic oxidation and reduction of the keto functional group with concomitant dehydration of the alcohol led to the formation of <strong>19</strong>,which after deprotection of</em> the carboxyl group followed by lactonization, gave the mellein-type 3,4-dihydroisocoumarin <strong>39</strong>.</p> ER -