Evaluation of the photodecarbonylation of crystalline ketones for the installation of reverse prenyl groups on the pyrrolidinoindoline scaffold
Evaluation of the photodecarbonylation of crystalline ketones for the installation of reverse prenyl groups on the pyrrolidinoindoline scaffold
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DOI：
10.1016/j.tet.2020.131181
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发表时间：
2020-12-18
期刊：
影响因子：
2.1
通讯作者：
Garcia-Garibay, Miguel A.
中科院分区：
文献类型：
--
作者：
Dotson, Jordan J.;Garg, Neil K.;Garcia-Garibay, Miguel A.
我们报告的区域控制安装的异戊二烯基部分在debroflustramine A的异戊二烯取代酮的区域特异性光脱羰基合成的努力。评价了从色胺开始获得合理的光脱羰底物的合成方法。最初尝试合成一个合适的基板光脱羰阻碍了基板结晶度（固态光化学的先决条件）的缺乏。最终，可以通过明智地选择N-取代基来获得结晶基底以尝试关键步骤。虽然光脱羰没有导致所需的反向异戊烯化，这项研究强调了晶相光化学所需的故障排除和优化，并强调了可用于控制基板结晶度的方法。(C)2020爱思唯尔有限公司版权所有。
We report synthetic efforts toward the regiocontrolled installation of the prenyl moiety in debromoflustramine A by the regiospecific photodecarbonylation of a prenyl-substituted ketone. Synthetic approaches to access the plausible photodecarbonylation substrates beginning from tryptamine were evaluated. Initial attempts to synthesize a suitable substrate for photodecarbonylation were hampered by a lack of substrate crystallinity (a prerequisite for solid-state photochemistry). Ultimately, a crystalline substrate could be accessed to attempt the key step by judicious selection of N-substituents. Although the photodecarbonylation did not result in the desired reverse prenylation, this study highlights the troubleshooting and optimization required for crystal phase photochemistry and underscores methods that can be used to control substrate crystallinity. (C) 2020 Elsevier Ltd. All rights reserved.