Yamada F
Faculty of Pharmaceutical Sciences, Kanazawa University, Japan.
Yakugaku Zasshi. 2000 Apr;120(4):363-73. doi: 10.1248/yakushi1947.120.4_363.
In our continuing work on synthesizing 4-substituted indole alkaloids as simple as possible by creating suitable reactions, we developed synthetic methods for 4-substituted indoles having a nitrogen or oxygen functional group at the 4-position starting from indole-3-carbaldehyde and one step conversion method of indole-3-carbaldehydes into indole-3-acetonitriles. Utilizing them, we could establish a practical synthetic route to 1,3,4,5-tetrahydropyrrolo[4,3,2-de]-quinoline in three steps from indole-3-carbaldehyde. On the basis of these results, short step total syntheses of marine indole alkaloids, such as isobatzelline C, batzelline C, makaluvamine A, and damirones A and B, were achieved. Furthermore, a novel preparative method of psilocin was established in only five steps from indole-3-carbaldehyde. The syntheses of psilocin analogs having a formyl group or bromine in the benzene part were also achieved.
在我们持续开展的通过创造合适反应尽可能简便地合成4-取代吲哚生物碱的工作中，我们开发了从吲哚-3-甲醛出发合成4-位带有氮或氧官能团的4-取代吲哚的方法，以及将吲哚-3-甲醛一步转化为吲哚-3-乙腈的方法。利用这些方法，我们能够从吲哚-3-甲醛出发，通过三步建立一条通往1,3,4,5-四氢吡咯并[4,3,2- de]喹啉的实用合成路线。基于这些结果，实现了海洋吲哚生物碱如异巴泽林C、巴泽林C、马卡鲁胺A以及达米罗宁A和B的短步骤全合成。此外，从吲哚-3-甲醛出发仅通过五步就建立了一种新的裸盖菇素制备方法。还实现了在苯部分带有甲酰基或溴的裸盖菇素类似物的合成。
