8.ストリゴラクトン基本骨格の簡易合成法(口頭発表)

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Strigolactones (SL) are a group of terpenoid lactones which promote seed germination of the parasitic plants Striga and Orobanche, and trigger the hyphal branching of arbuscular mycorrhizal fungi. Recent studies suggest that SL act as a new plant hormone that inhibits shoot branching in plants. In SL molecules, the structure of a lactone (the C-ring), a butyrolactone (the D-ring) and an enol ether bridge connecting these rings are universally included, whereas all known SL possess one or two methyl groups on the cyclohexyl A-ring and various combination of hydroxyl or acetate substituents around the A- and B-rings. Therefore, 5-deoxystrigol having two methyl groups on the A-ring and no oxygen function in the AB-rings is supposed to be the precursor of all the different SL produced by further chemical and/or enzymatic modifications. To prepare 5-deoxystrigol to be used as a biochemical tool for investigating the biosynthesis of SL, we synthesized the ABC-part of the compound by simple method. A (hydroxypropynyl) cyclohexanol was prepared from the cyclohexanone and propargyl alcohol, which was cyclized to the bicyclic enone (the AB-rings) with methanesulfonic acid in acetic acid. The enone was converted to the oxo acid in three steps. The oxo acid was thus reduced, and the resulting hydroxy acid was lactonized to give the ABC-part of 5-deoxystrigol with a total yield of 24%. This simple method could promote the synthesis of AB-rings-modified strigolactones.
植物化学調節学会の論文
2008-10-06

8.ストリゴラクトン基本骨格の簡易合成法(口頭発表)

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