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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.

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。
Org Lett. 2020 Jan 3;22(1):168-174. doi: 10.1021/acs.orglett.9b04119. Epub 2019 Dec 13.
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Org Lett. 2011 Feb 18;13(4):740-3. doi: 10.1021/ol102980t. Epub 2011 Jan 19.
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Concise Synthesis of the Xenibellols Core.西尼贝醇核心结构的简洁合成
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