P-62 Panepophenanthrinの不斉全合成及びその構造活性相関(ポスター発表の部)

概要

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The asymmetric total synthesis of (+)-panepophenanthrin (1), an inhibitor of ubiquitin-activating enzyme (E1), has been accomplished using proline-catalyzed asymmetric a-aminoxylation and the biomimetic Diels-Alder reaction as key steps. Asymmetric α-aminoxylation of 1,4-cyclohexanedione monoethylene ketal (6) in the presence of D-proline with nitrosobenzene gave (S)-α-aminoxylated cyclohexanone (5). After several diastereoselective reactions, the key intermediate 4 was obtained. The monomer 2 was synthesized by Stille coupling reaction of 4 with vinyl stannane 14, followed by removal of the silyl protecting group. The biomimetic Diels-Alder reaction of the monomer 2 was found to proceed efficiently under neat condition or in water. The investigation of the biological properties of new derivatives of (+)-panepophenanthrin (1) enabled us to develop new cell-permeable E1 inhibitors, RKTS-80 (21), -81 (22), and -82 (23).
天然有機化合物討論会の論文
2007-08-24