53 海産抗腫瘍性アルカロイドマンザミン類の合成研究(口頭発表の部)
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概要
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The manzamine family of marine alkaloids was isolated from several Okinawan marine sponges by Higa and later by Nakamura, while the new and biogenetically related alkaloid ircinals have been isolated by Kobayashi quite recently. The first isolated congener manzamine A (1) and manzamine B(2), a presumed biogenetic precursor to 1, have been the subject of recent synthetic investigations owing to its unique molecular structure and remarkable biological properties including antitumor and antibacterial activities. We have set out our synthetic approach towards these structurally intriguing and biologically interesting alkaloids and, at the outset, we have selected the simplest congener manzamine C (3) and related analogs as our initial targets, especially in order to clarify its structure-activity relationships. Thus, according to the general synthetic route shown in Scheme IV, we have synthesized natural manzamine C (3), its trans-isomer (23) and various analogues with saturated azacyclic ring (22). The in vitro biological evaluations of these compounds revealed that the azacyclic anlogues also exhibit comparable activity to 3. For the challenging construction of the central azacyclic cores of 1 and 2, we envisaged the retrosynthetic scheme shown in Scheme V, which is featured by the utilization of a Diels-Alder reaction of 3-alkyl-5,6-dihydro-2-pyridinones under suitably optimized conditions. The synthetic problems we encountered here were 1) efficient preparation of the dienophiles 2) optimization of the conditions for the crucial Diels-Alder reaction 3) effective removal of the protecting groups and further transformation. Proper solutions to these problems are shown in Scheme VI〜IX and we have successfully obtained a precursor (57) to the tetracyclic system of manzamine A (1).
- 天然有機化合物討論会の論文
- 1992-09-10
著者
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中川 昌子
千葉大薬
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日野 亨
千葉大 薬
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橋本 彰宏
Faculty of Pharmaceutical Sciences, Chiba University
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鳥澤 保廣
千葉大・薬
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鳥澤 保廣
千葉大薬
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橋本 彰宏
千葉大薬
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保坂 俊弘
千葉大薬
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田辺 潔
千葉大薬
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Tavet Fabrice
千葉大薬
-
日野 亨
千葉大薬
-
中川 昌子
千葉大 薬
-
橋本 彰宏
Faculty Of Pharmaceutical Sciences Chiba University
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