A Biosynthetically-Inspired Chemical Synthesis of Naturally Occurring Halogenated Medium Ring Ethers from Laurencia

劳伦西亚天然卤化中环醚的生物合成启发化学合成

• 批准号: EP/F034253/1
• 负责人: David Braddock
• 金额: $ 40.27万
• 依托单位: Imperial College London
• 依托单位国家: 英国
• 项目类别: Research Grant
• 财政年份: 2008
• 资助国家: 英国
• 起止时间: 2008 至 无数据
• 项目状态: 已结题
• 来源: https://gtr.ukri.org/projects?ref=EP%2FF034253%2F1
• 关键词: Biosynthetically; Inspired; Chemical; Synthesis; Naturally

Seaweeds and alga provide a rich source of naturally occurring bromine and chlorine (halogenated) containing natural products. In particular, Laurencia species provide such halogenated compounds as medium ring ethers (rings of 7,8 or 9-atoms consisting of one oxygen and the rest as carbon) that have traditionally been viewed as difficult to synthesize in a laboratory. Previously, the biogenesis of these compounds has been assumed to involve the cyclisation of an alcohol onto a reactive bromonium ion to create the medium ring. However, there are some unexplained difficulties with the currently proposed biogenesis. We now propose that alcohols are not the true biogenetic precursors. Consideration of the various configurations of the metabolites from Laurencia species allows a unifying biosynthetic scheme to be proposed from an alternative common precursor, which are spring-loaded to overcome the traditional difficulties associated with making medium-sized rings.

海藻和海藻提供了天然存在的含溴和氯（卤化）的天然产物的丰富来源。特别地，凹顶藻属物种提供了这样的卤代化合物作为中环醚（由一个氧和其余的碳组成的7、8或9个原子的环），其传统上被认为难以在实验室中合成。以前，这些化合物的生物成因被认为涉及醇环化到活性溴离子上以产生中环。然而，目前提出的生物成因存在一些无法解释的困难。我们现在提出醇类不是真正的生物前体。从凹顶藻物种的代谢产物的各种配置的考虑允许一个统一的生物合成方案，提出从一个替代的共同的前体，这是弹簧加载，以克服传统的困难，使中等大小的环。