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通过伯吉斯试剂在酸性条件下介导δ-二醇的环脱水反应合成氧杂双环[3.2.1]辛烷-3-醇骨架

Synthesis of Oxabicyclo[3.2.1]octan-3-ol Scaffold via Burgess Reagent Mediated Cyclodehydration of δ-Diols under Acidic Conditions.

作者信息

Elmansy Mohamed F, Dos Remedios Jose Ricardo D, Silverman Richard B

机构信息

Department of Chemistry, Department of Molecular Biosciences, Chemistry of Life Processes Institute, Center for Developmental Therapeutics, Northwestern University, Evanston, Illinois 60208-3113, United States.

Organometallic and Organometalloid Chemistry Department, National Research Centre, 12622 Cairo, Egypt.

出版信息

Org Lett. 2025 Jan 17;27(2):640-644. doi: 10.1021/acs.orglett.4c04473. Epub 2025 Jan 6.

DOI:10.1021/acs.orglett.4c04473
PMID:39761354
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11901898/
Abstract

Dehydrative cyclization of δ-diols was achieved by using the Burgess reagent under mild conditions to furnish a novel oxabicyclo[3.2.1]octan-3-ol scaffold. The stereochemistry of the generated oxabicyclic compounds was assigned based on single X-ray crystallography and 2D-NMR experiments.

摘要

在温和条件下，使用伯吉斯试剂实现了δ-二醇的脱水环化反应，得到了一种新型的氧杂双环[3.2.1]辛-3-醇骨架。基于单晶X射线晶体学和二维核磁共振实验确定了所生成的氧杂双环化合物的立体化学结构。

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本文引用的文献

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Catalytic Sulfamoylation of Alcohols with Activated Aryl Sulfamates.醇的活化芳基磺酰胺的催化磺酰化反应。
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Chiral cyclohexane 1,3-diones as inhibitors of mutant SOD1-dependent protein aggregation for the treatment of ALS.手性环己烷1,3 - 二酮作为突变型超氧化物歧化酶1依赖性蛋白质聚集的抑制剂用于治疗肌萎缩侧索硬化症。
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Cyclohexane 1,3-diones and their inhibition of mutant SOD1-dependent protein aggregation and toxicity in PC12 cells.环己烷 1,3-二酮及其对 PC12 细胞中突变型 SOD1 依赖性蛋白聚集和毒性的抑制作用。
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Feuding rule makers: Aleksandr Mikhailovich Zaitsev (1841-1910) and Vladimir Vasil'evich Markovnikov (1838-1904). A commentary on the origins of Zaitsev's rule.相互争执的规则制定者：亚历山大·米哈伊洛维奇·扎伊采夫（1841 - 1910）和弗拉基米尔·瓦西里耶维奇·马尔科夫尼科夫（1838 - 1904）。关于扎伊采夫规则起源的评论
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Cyclopropenium-activated cyclodehydration of diols.环丙烯鎓促进的二醇环脱水反应。
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8
Concise Synthesis of the Xenibellols Core.西尼贝醇核心结构的简洁合成
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Total synthesis of prostaglandin-E2 by rearrangement of a 6,8-disubstituted-2-oxabicyclo[3.2.1]octan-3-one to a 4,5 disubstituted-perhydrocyclopenta[b]furan-2-one.通过将6,8 - 二取代 - 2 - 氧杂双环[3.2.1]辛烷 - 3 - 酮重排为4,5 - 二取代 - 全氢环戊并[b]呋喃 - 2 - 酮来全合成前列腺素 - E2 。
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