13-环氧壬基氧化物的一步选择性合成

IF 0.5 Q4 CHEMISTRY, MULTIDISCIPLINARY

Chemistry Journal of Moldova Pub Date : 2021-05-01 DOI:10.19261/CJM.2021.820

O. Morarescu, Marionela Traistari, A. Barba, G. Duca, N. Ungur, V. Kulcițki

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引用次数: 2

摘要

报道了以巩膜醇低温超酸性环化为基础，一步选择性合成了13-环氧壬基氧化物。对反应条件进行了精细的调整，以使外聚物氧化物之间的比例达到9:1，有利于所需的13-外聚物氧化物。氢、碳核磁共振证实了产物的结构，气相色谱-质谱分析了产物的组成。这些结果可以用假设的SN2机制来解释，该机制发生在起始底物的C-13手性中心附近的构型反转。在克级实验中证明了该工艺的制备价值。

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One-step Selective Synthesis of 13-epi-manoyl Oxide

The selective one-step synthesis of 13-epi-manoyl oxide is reported based on a low-temperature superacidic cyclization of sclareol. The reaction conditions have been finely tuned in order to achieve a 9:1 ratio between epimeric oxides in favour of the desired 13-epi-oxide. The structures were confirmed by H and C NMR, and composition of the crude reaction products determined by GC-MS. These results have been interpreted by a hypothetical SN2 mechanism which occurs with inversion of configuration around the C-13 chiral center of the starting substrate. The preparative value of the elaborated procedure is demonstrated on a gram-scale experiment.

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来源期刊

Chemistry Journal of Moldova CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

0.90

自引率

20.00%

发文量

审稿时长

12 weeks

期刊介绍： "Chemistry Journal of Moldova. General, Industrial and Ecological Chemistry" seeks to publish experimental or theoretical research results of outstanding significance and timeliness in all fields of Chemistry, including Industrial and Ecological Chemistry. The main goal of this edition is strengthening the Chemical Society of Moldova, following development of research in Moldovan chemical institutions and promotion of their collaboration with international chemical community. Manuscripts are welcome from all countries.