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Studies towards Trichodimerol: Novel Cascade Reactions and Polycyclic Frameworks

机译:对天花粉醇的研究:新型级联反应和多环框架

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摘要

Trichodimerol (1) is a synthetically attractive natural product because of its potential medical use against septic shock and its striking molecular architecture. We report herein the possible biosynthetic pathway for its formation from the hexaketide sorbicillin (3) and our preliminary results towards the total synthesis of trichodimerol (1) and its congener demethyltrichodimerol (2). These studies provided a way to synthesize #beta#-ketal ketones by a novel variation of the Mukaiyama Aldol reaction, afforded new insight into the mild and regioselective formation of silyl enol ethers, and allowed the preparation of the advanced intermediate 38. Furthermore, a number of unprecedented cascade reactions were discovered furnishing novel polycyclic, highly oxygenated compounds from simple starting materials.
机译:Trichodimerol(1)是一种具有吸引力的天然合成产品,因为其潜在的医学用途可抵抗败血性休克及其惊人的分子结构。我们在这里报告了可能的生物合成途径,从六酮类山梨醇(3)形成它,并且我们初步的结果是向总的合成了trichodimerol(1)及其同类物demethyltrichodimerol(2)。这些研究提供了一种通过Mukaiyama Aldol反应的新颖变化来合成#β#-缩酮的方法,提供了对甲硅烷基烯醇醚的轻度和区域选择性形成的新见解,并允许制备高级中间体38。发现了许多前所未有的级联反应,它们可以从简单的起始原料中制备出新颖的多环,高度氧化的化合物。

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