87 光学活性2-フリルカルビノールを用いるラクトン系抗生物質の合成(口頭発表の部)

概要

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2-Furylcarbinols(1), which could be converted into the 2-substituted 6-hydroxy-2H-pyran-3(6H)-ones(2) by oxidative methods, would be well suited as starting materials for the synthesis of a variety of physiologically active compounds. Chemical modification of all carbons on pyran ring can be easily achieved in stereo-controlled manners owing to the functionality presented in 2. We have demonstrated transformation of chiral 2-furylcarbinols into lactonic antibiotics via the pyranones. Enantioselective syntheses of 6-substituted 5,6-dihydro-2H-pyran-2-ones, (+)-acetylphomalactone(9) and (+)-goniothalamin(10), have been carried out employing kinetic resolution of racemic secondary 2-furylcarbinols(3,4). An enantioselective synthesis of (-)-canadensolide(33),an antifungal mold metabolite, has been accomplished using sequential stereoselective reduction of the pyranone(22) as key steps. We have also achieved an enantioselective synthesis of (-)-malyngolide(45), a marine antibiotic, using a diastereoselective addition reaction of nonylmagnesium bromide to the 2-acylfuran(36) as a crucial step.
天然有機化合物討論会の論文
1990-09-25