A concise stereoselective synthesis of pterosin B
A concise stereoselective synthesis of pterosin B
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DOI：
10.1016/j.tetlet.2018.10.056
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发表时间：
2018-12-05
影响因子：
1.8
通讯作者：
Williams, David M.
中科院分区：
文献类型：
--
作者：
Dexter, Hannah R.;Allen, Esther;Williams, David M.
Pterosin B是一种在蕨类植物中发现的天然吲哚酮，具有多种有趣的药理特性，但很少有立体选择性合成。本文描述了以6-溴-5,7-二甲基林丹-1- 1为原料合成(2R)-翼鸟色素B的7步立体选择性反应，其结构通过NOE分析和x射线晶体学测定得到了证实。通过Suzuki-Miyaura交叉偶联反应引入羟基乙基链。通过甲基化SAMP [(S)-1-氨基-2-甲氧基-甲基)吡啶]腙立体选择性引入2-甲基，去除手性辅助物生成(2R)-pterosin B。pterosin B的结构通过特定旋光度和x射线晶体学测定得到。爱思唯尔有限公司2018年版权所有
Pterosin B is a naturally occurring indanone found in bracken fern (Pteridium aquilinum) that displays a variety of interesting pharmacological properties, but for which few stereoselective syntheses exist. Herein we describe a 7-step stereoselective synthesis of (2R)-pterosin B via 6-bromo-5,7-dimethylindan-1-one whose structure was confirmed by NOE analysis and structure determination by X-ray crystallography. The hydroxyethyl chain was introduced via a Suzuki-Miyaura cross-coupling reaction. The 2-methyl group was introduced stereoselectively by methylation of a SAMP [(S)-1-amino-2-methoxy-methyl)pyrrolidine] hydrazone and the chiral auxiliary was removed to produce (2R)-pterosin B. The structure of pterosin B was confirmed by specific rotation and structural determination by X-ray crystallography. Crown Copyright (C) 2018 Published by Elsevier Ltd.