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The first total synthesis of marine natural product, (−)-majusculoic acid (<b>1</b>) and its seven analogs (<b>9</b>–<b>15</b>), was accomplished in three to ten steps with a yield of 3% to 28%. The strategy featured the application of the conformational controlled establishment of the <i>trans</i>-cyclopropane and stereochemical controlled bromo-olefination or olefination by Horner–Wadsworth–Emmons (HWE) reaction. The potential anti-inflammatory activity of the eight compounds (<b>1</b> and <b>9</b>–<b>15</b>) was evaluated by determining the nitric oxide (NO) production in the lipopolysaccharide (LPS)-induced mouse macrophages RAW264.7. (−)-Majusculoic acid (<b>1</b>), methyl majusculoate (<b>9</b>), and (1<i>R</i>,2<i>R</i>)-2-((3<i>E</i>,5<i>Z</i>)-6-bromonona-3,5-dien-1-yl)cyclopropane-1-carboxylic acid (<b>12</b>) showed significant effect with inhibition rates of 33.68%, 35.75%, and 43.01%, respectively. Moreover, they did not show cytotoxicity against RAW264.7 cells, indicating that they might be potential anti-inflammatory agents.