Enantioselective Total Synthesis of Cannabinoids via a Tandem Conjugate Addition/Enolate Alkylation Annulation with Ambiphilic Organoboronates
Enantioselective Total Synthesis of Cannabinoids via a Tandem Conjugate Addition/Enolate Alkylation Annulation with Ambiphilic Organoboronates
复制标题
通过串联共轭加成/烯醇烷基化与两亲性有机硼酸酯对映选择性全合成大麻素
DOI：
10.1021/acs.orglett.3c00090
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发表时间：
2023
期刊：
影响因子：
5.2
通讯作者：
May, Jeremy A.
中科院分区：
文献类型：
--
作者：
Luo, Jirong;May, Jeremy A.
大麻素的研究依赖于合成衍生物进行构效关系研究。（−）-Δ9-四氢大麻酚和大麻二酚是通过串联的对映选择性共轭加成/烯醇化物烷基化环化反应与一种新型的两亲性三氟硼酸盐在七个步骤中合成的。合成了一类新的烯基和芳基两亲性三氟硼酸酯，并显示出与各种官能团的良好相容性，高产率，以及优异的对映体和非对映体选择性。合成了一种新型的苯并稠合大麻素类似物和串联的含四元立体中心的反应产物，具有良好的对映选择性。
Cannabinoid research depends on synthesizing derivatives for structure–activity relationship studies. (−)-Δ9-Tetrahydrocannabinol and cannabidiol were synthesized via a tandem enantioselective conjugate addition/enolate alkylation annulation with a novel ambiphilic trifluoroborate in seven steps. A new class of alkenyl and aryl ambiphilic trifluoroborates were synthesized and showed great compatibility with various functional groups, high yields, and excellent enantio- and diastereoselectivity. A novel benzo-fused cannabinoid analogue and tandem quaternary stereocenter-containing reaction products were synthesized with good to excellent enantioselectivity.