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单亚烷基二酮哌嗪的合成及其在巴瑞替尼合成中的应用。

Synthesis of monoalkylidene diketopiperazines and application to the synthesis of barettin.

作者信息

Kelley Elizabeth W, Norman Skylar G, Scheerer Jonathan R

机构信息

Department of Chemistry, The College of William & Mary, P.O. Box 8795, Williamsburg, Virginia 23187, USA.

出版信息

Org Biomol Chem. 2017 Oct 18;15(40):8634-8640. doi: 10.1039/c7ob02297b.

DOI:10.1039/c7ob02297b
PMID:28980696
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5678964/
Abstract

The synthesis of barettin, a selective serotonin receptor inhibitor and potent antibiofouling natural product, is described. The synthesis starts with the diketopiperazine nucleus intact and the side chains are installed using iterative aldol condensations. The route represents a general strategy for synthesis of a wide array of mono-alkylidene diketopiperazine structures, including those derived from non-canonical amino acid residues.

摘要

本文描述了巴雷廷(一种选择性5-羟色胺受体抑制剂和强效抗生物污损天然产物)的合成。合成从完整的二酮哌嗪核开始,通过迭代羟醛缩合反应安装侧链。该路线代表了一种合成多种单亚烷基二酮哌嗪结构的通用策略,包括那些源自非标准氨基酸残基的结构。

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