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多克规模(±)-ambrenolide 的非对映选择性聚烯环化全合成。

Multigram-scale total synthesis of (±)-ambreinolide by a diastereoselective polyene cyclization.

机构信息

Friedrich-Schiller-Universität Jena, Institut für Organische Chemie und Makromolekulare Chemie, Humboldtstr. 10, D-07743 Jena, Germany.

Friedrich-Schiller-Universität Jena, Institut für Anorganische und Analytische Chemie, Humboldtstr. 8, D-07743 Jena, Germany.

出版信息

Bioorg Med Chem Lett. 2022 Sep 15;72:128845. doi: 10.1016/j.bmcl.2022.128845. Epub 2022 Jun 11.

Abstract

Ambreinolide is a natural terpenoid with great value for perfume industry and natural product synthesis. Herein we report a novel total synthesis of ambreinolide on multigram-scale that employs a regio- and diastereoselective, high yielding, proton-initiated polyene cyclization using a catalyst easily generated in situ. Molecular structures were unambiguously confirmed by X-ray crystallography.

摘要

龙涎香醇是一种具有重要价值的天然萜烯,在香水行业和天然产物合成中具有广泛的应用。在此,我们报告了一种新型的龙涎香醇的全合成方法,该方法采用区域和立体选择性、高产率的质子引发的多烯环化反应,使用易于原位生成的催化剂。通过 X 射线晶体学分析,明确了分子结构。

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