首页> 外文期刊>Organic letters >Biosynthetically Inspired Divergent Approach to Monoterpene Indole Alkaloids: Total Synthesis of Mersicarpine, Leuconodines B and D, Leuconoxine, Melodinine E, Leuconolam, and Rhazinilam
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Biosynthetically Inspired Divergent Approach to Monoterpene Indole Alkaloids: Total Synthesis of Mersicarpine, Leuconodines B and D, Leuconoxine, Melodinine E, Leuconolam, and Rhazinilam

机译:单萜吲哚生物碱的生物合成启发性方法:梅西卡品,亮二烯丁二烯和丁二烯,亮三恶英,Melodinine E,亮三烯和Rhazinilam的全合成

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摘要

Inspired by their potential biosynthesis, we have developed divergent total syntheses of seven monoterpene indole alkaloids including mersicarpine, leuconodines B and D, leuconoxine, melodinine E, leuconolam, and rhazinilam, and one unnatural analogue with an unprecedented structural skeleton. The key steps involve a Witkop-Winterfeldt oxidative indole cleavage followed by transannular cyclization. The transannular cyclization product was then converted to the corresponding structural skeletons by pairing its functional groups into different reaction modes.
机译:受其潜在生物合成的启发,我们开发了七种单萜吲哚生物碱的不同总合成物,其中包括美西卡平,亮二酮B和D,亮氨新碱,美洛地宁E,亮氨酸和鼠李素,以及一种具有前瞻性结构骨架的非天然类似物。关键步骤涉及Witkop-Winterfeldt氧化吲哚裂解,然后经环环化。然后通过将跨环环化产物的官能团配对成不同的反应模式,将其转化为相应的结构骨架。

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