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可见光促进的串联硫醇-烯点击反应/环加成反应和区域选择性环丙烷开环构建含硫二萜。

Visible-Light-Promoted Tandem Thiol-Ene Click Reaction/Transannular Cyclization and Regioselective Cyclopropane Ring-Opening to Construct Sulfur-Containing Diterpenes.

机构信息

School of Life Science and Engineering, Southwest Jiaotong University, Chengdu, Sichuan 610031, People's Republic of China.

Department of Microbiology, Immunology and Transplantation, Rega Institute for Medical Research, Laboratory of Virology and Chemotherapy, KU Leuven, Herestraat 49, Box 1043, 3000 Leuven, Belgium.

出版信息

Org Lett. 2023 Feb 3;25(4):597-602. doi: 10.1021/acs.orglett.2c04116. Epub 2023 Jan 20.

Abstract

The biorelevant sulfur-containing diterpenes with scarce 5/7/6/3 premyrsinane- and 5/7/6 myrsinane-type backbones were easily constructed from naturally abundant lathyrane-type factor L by visible-light-triggered tandem thiol-ene click reaction/transannular cyclization and regioselective cyclopropane ring-opening. The selenide diterpene was also successfully obtained to verify the system universality. This concise synthesis route gives an efficient strategy for obtaining structurally diverse diterpenes under very mild conditions and provides a promising anti-HIV bioactive premyrsinane diterpene .

摘要

具有生物相关含硫的罕见 5/7/6/3 前迈尔斯烷型和 5/7/6 迈尔斯烷型骨架的二萜类化合物很容易通过可见光触发的硫醇-烯点击反应/环丙烷开环串联反环化,从天然丰富的拉坦烷型因子 L 构建得到。硒代二萜也成功获得,以验证该体系的通用性。这种简洁的合成路线为在非常温和的条件下获得结构多样的二萜类化合物提供了有效的策略,并为具有抗 HIV 生物活性的前迈尔斯烷二萜类化合物提供了有前景的候选药物。

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