怀克辛辛A的合成:探索九个成员环形形成的策略
Christian Steinborn1, Tatjana Huber2, Julian Lichtenegger1
1Institute of Organic Chemistry and Center for Molecular Biosciences, University of Innsbruck, Innrain 80-82, 6020, Innsbruck, Austria.
Chemistry (Weinheim an der Bergstrasse, Germany)
|November 9, 2023
概括
研究人员详细介绍了waixenicin A的合成,克服了使用新策略构建其复杂的九个环的挑战,并实现了关键的中间构成.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
- 自然产品的合成自然产品的合成
背景情况:
- 色素A是一种复杂的天然产品,具有独特的6/9循环结构.
- 这种复杂分子的合成在立体化学控制和环形形成方面提出了重大挑战.
研究的目的:
- 为waixenicin A.探索的合成策略提供一个全面的描述.
- 详细说明在综合过程中遇到的挑战和开发的解决方案.
- 报告waixenicin A和相关化合物的成功合成.
主要方法:
- 阿克马托维奇对二胺环结构的重新排列.
- 对九个环组件的四种不同的策略的研究.
- 探讨基于基的反应,阳离子碎片化,诺扎基-希亚马-基希,赫克反应和分子内化.
主要成果:
- 针对C7-C11和C6-C7债券的初始策略没有成功地形成6/9自行车.
- 阴离子分裂导致了5/9自行车,但随后的环扩张失败了.
- 为C5-C6键实现了分子内化,但功能组修改具有挑战性.
- 构建C9-C10键被证明是成功形成九个环的关键策略,并合成了waixenicin A.
结论:
- 合成路线的重新设计是基于对各种债券结构的调查.
- 我们成功地合成了waixenicin A和9-deacetoxy-14,15-deepoxyxeniculin.
- 通过生物启发,将9-deacetoxy-14,15-deepoxyxeniculin重新排列成xeniafauranol A已经完成.
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