The Witkop reaction: A Photochemical C-H-activation/cyclization and its Strategic Application in the Total Synthesis of Dichomine and related Alkaloids

Witkop 反应：光化学 C-H 激活/环化及其在二氯碱和相关生物碱全合成中的战略应用

• 批准号: 282720274
• 负责人: Professorin Dr. Tanja Gaich
• 金额: --
• 依托单位: Arbeitsgruppe Naturstoffchemie/Totalsynthese
• 依托单位国家: 德国
• 项目类别: Research Grants
• 财政年份: 2015
• 资助国家: 德国
• 起止时间: 2014-12-31 至 2019-12-31
• 项目状态: 已结题
• 来源: https://gepris.dfg.de/gepris/projekt/282720274?language=en
• 关键词: Witkop; reaction; Photochemical; activation; cyclization

Investigations of excited-state redox processes have an exceptional impact on the field of organic photochemistry and its application to the synthesis of complex target molecules. The Witkop cyclization constitutes an intramolecular variant of such a process typically with an indole heterocycle as electron donor. The following proposal details the application of this reaction to the total synthesis of dichomine and related natural products. The synthetic plans devised in this project are based on our earlier works on leuconoxine. Application of this photoreaction to these natural products will represent a showcase for the potential of this transformation and is of vital importance for the efficient access to these alkaloids.

激发态氧化还原过程的研究对有机光化学领域及其在复杂目标分子合成中的应用具有特殊的影响。Witkop环化反应构成了这一过程的分子内变体 通常以吲哚杂环作为电子供体。以下建议详细介绍了该反应在全合成双草胺及相关天然产物中的应用。本项目的合成方案是基于我们早期对明可诺辛的研究。将这种光反应应用于这些天然产物将代表这种转化潜力的展示，并且对于有效获得这些生物碱至关重要。

项目成果

Total synthesis of (±)-20S-hydroxy-1,2-dehydro-pseudoaspidospermidine via a C-H activation/transannular cyclization strategy.

通过C-H活化/跨环环化策略全合成(±)-20S-羟基-1,2-脱氢-拟蜘蛛亚精胺

• DOI: 10.1039/c7cc02699d
• 发表时间: 2017
• 期刊: Chemical communications
• 影响因子: 4.9
• 作者: C. Leitner;T. Gaich
• 通讯作者: T. Gaich