33 Ajmaline及びIsoajmalineの合成研究
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概要
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A synthesis of rac-ajmaline and -isoajmaline is described. As a preliminary to the synthesis of ajmaline-sarpagine group of alkaloids, Yoneda in our laboratory has recently reported a synthesis of compound (XVI) (Chart-I), representing the fundamental skeleton of the abovementioned alkaloids. In a model experiment for our present study, we converted the intermediate compound (VIIIa) in the above synthesis to (XVIII) by applying Corey's method followed by HAlCl_2 reduction. For the synthesis of ajmaline (VIIIa) was first cyanomethylated to furnish (XIX) (Chart-2), which was then treated as above to give (XXIII). The latter was proved to be identical with the intermediate (XXVIIIa) (Chart-3) in Masamune's elegant total synthesis of ajmaline. Synthesis of isoajmaline was achieved by first introducing α-cyano-n-propyl side-chain to (VIIIa) to afford (XXXIII) (Chart-4) and processed similary to give (XXXVIII), which was found to be identical with the compound (XLIIa) (Chart-5) used as a relay substance prepared from isoajmaline.
- 天然有機化合物討論会の論文
- 1968-09-20
著者
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佐藤 泰彦
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
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真下 喜世彦
田辺製薬有機化学研究所
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佐藤 泰彦
田辺製薬有機化学研究所
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