Morikawa Hiroshi, Yamaguchi Jun-Ichi, Sugimura Shun-Ichi, Minamoto Masato, Gorou Yuuta, Morinaga Hisatoyo, Motokucho Suguru
Department of Applied Chemistry, Kanagawa Institute of Technology, 1030, Shimo-ogino, Atsugi, Kanagawa 243-0292, Japan.
Faculty of Education, Graduate Faculty of Interdisciplinary Research, University of Yamanashi, 4-4-37, Takeda, Kofu, Yamanashi 400-8510, Japan.
Beilstein J Org Chem. 2019 Jan 14;15:130-136. doi: 10.3762/bjoc.15.13. eCollection 2019.
In order to produce versatile and potentially functional terpene-based compounds, a ()-limonene-derived diol and its corresponding five-membered cyclic carbonate were prepared. The diol (cyclic carbonate) comprises four diastereomers based on the stereochemical configuration of the diol (and cyclic carbonate) moiety. By choosing the appropriate starting compounds (- and -limonene oxide) and conditions, the desired diastereomers were synthesised in moderate to high yields with, in most cases, high stereoselectivity. Comparison of the NMR data of the obtained diols and carbonates revealed that the four different diastereomers of each compound could be distinguished by reference to their characteristic signals.
为了制备多功能且具有潜在功能的萜烯基化合物，制备了一种由（）-柠檬烯衍生的二醇及其相应的五元环状碳酸酯。基于二醇（和环状碳酸酯）部分的立体化学构型，该二醇（环状碳酸酯）包含四种非对映异构体。通过选择合适的起始化合物（-和-氧化柠檬烯）和条件，以中等到高的产率合成了所需的非对映异构体，在大多数情况下具有高立体选择性。对所得二醇和碳酸酯的核磁共振数据进行比较表明，每种化合物的四种不同非对映异构体可以通过参考其特征信号来区分。
