A new synthesis of gelsemine using a novel bridge-swapping strategy

使用新型桥交换策略合成钩吻碱

• 批准号: EP/D010233/1
• 负责人: Nigel Simpkins
• 金额: $ 25.12万
• 依托单位: University of Nottingham
• 依托单位国家: 英国
• 项目类别: Research Grant
• 财政年份: 2006
• 资助国家: 英国
• 起止时间: 2006 至 无数据
• 项目状态: 已结题
• 来源: https://gtr.ukri.org/projects?ref=EP%2FD010233%2F1
• 关键词: new; synthesis; gelsemine; using; novel

The synthesis of compact, densely functionalised, polycyclic natural products remains a challenge to synthetic chemists, and an important stimulus for the development of new synthetic methodology and strategies. The complex alkaloid target gelsemine is regarded as a classic challenge for organic synthesis, but despite attracting the attention of numerous research groups over the years only seven total syntheses have been accomplished, and these proceed by long (typically ca. 25 steps, with the shortest being around 18 steps) and largely inefficient routes. We plan to develop a new strategy (and some novel chemistry) that would enable a very short (maybe as few as 10 steps) new synthesis of this molecule. This would generate a new 'landmark' contribution to the area, as well as establishing more generally applicable synthetic chemistry.

合成紧凑，密集功能化，多环的天然产物仍然是一个挑战，合成化学家，并为新的合成方法和策略的发展的重要刺激。复杂的生物碱目标钩吻碱被认为是有机合成的经典挑战，但尽管多年来吸引了众多研究小组的注意，但只有七个总的合成已经完成，并且这些合成进行了很长时间（通常约为20分钟）。25步，最短的是18步左右）和效率很低的路线。我们计划开发一种新的策略（和一些新的化学方法），使这种分子的新合成非常短（可能只有10个步骤）。这将对该领域产生新的“里程碑式”贡献，并建立更普遍适用的合成化学。

项目成果

Asymmetric Deprotonations using Chiral Lithium Amide Bases

使用手性氨基锂碱的不对称去质子化

• 发表时间: 2010
• 期刊: Topics in Stereochemistry
• 作者: N/a Weller