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Synthesis from Δ3-Carene of Optically Active Macrolides with Fragments of Di- and Triethyleneglycol and Hydrazides of Dicarboxylic Acids
Chemistry of Natural Compounds ( IF 0.8 ) Pub Date : 2020-05-01 , DOI: 10.1007/s10600-020-03068-1
M. P. Yakovleva , K. S. Denisova , G. R. Mingaleeva , Yu. V. Myasoedova , L. R. Garifullina , N. M. Ishmuratova , G. Yu. Ishmuratov

Efficient syntheses of six potentially useful optically pure macroheterocycles with ester and dihydrazide fragments were developed from available natural Δ3-carene through intermediate (31R,33S)-32,32-dimethyl-3(1,3)cyclopropyla-5-oxohexanoic acid using in the key steps [2+1]-reactions of the last with di- or triethylene glycol and [1+1]-condensation of the resulting α,ω-diketodiesters with several dicarboxylic acid dihydrazides. The structures of the obtained compounds were confirmed by IR and NMR spectroscopy and LC-MS.

中文翻译:

从 Δ3-Carene 合成具有二和三乙二醇片段的光学活性大环内酯和二羧酸的酰肼

从可用的天然 Δ3-carene 到中间体 (31R,33S)-32,32-二甲基-3(1,3) 环丙α-5-氧代己酸,开发了六种具有酯和二酰肼片段的潜在有用的光学纯大杂环的有效合成关键步骤 [2+1] - 最后一个与二甘醇或三甘醇的反应以及所得 α,ω-二酮二酯与几种二羧酸二酰肼的 [1+1]-缩合。所得化合物的结构通过IR和NMR光谱以及LC-MS确认。
更新日期:2020-05-01
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