Synthesis and germination activity study of novel strigolactam/strigolactone analogues
Synthesis and germination activity study of novel strigolactam/strigolactone analogues
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DOI：
10.1016/j.tetlet.2022.154315
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发表时间：
2023-01-17
影响因子：
1.8
通讯作者：
Chen, Gang
中科院分区：
文献类型：
--
作者：
Ge, Yuhua;Chen, Xingyue;Chen, Gang
在此，我们报道了一种有效且实用的合成路线，以组装新型的高度-数十个[5，5]反式-稠合的B/C独脚金内酰胺/独脚金内酯类似物沿着与顺式-稠合的独脚金内酰胺。我们的合成策略的关键特征包括钯催化的羧酸盐定向烯化的市售N-Boc苯丙氨酸，然后直接光催化脱羧Giese环化。对新合成的支架材料进行了刺激列当库马纳种子萌发的构效关系研究。反式稠合化合物比顺式稠合化合物表现出更好的活性。然而，独脚金内酯35/36和39/40显示出比GR 245 DS和GR 244 DO上级的生物活性。(c)2022爱思唯尔有限公司保留所有权利。
Herein, we report an efficient and practical synthetic route to assemble novel highly-tens [5,5] trans- fused B/C strigolactam/strigolactone analogues along with cis-fused strigolactams. The key feature of our synthetic strategy includes palladium-catalyzed carboxylate-directed olefination of commercially available N-Boc phenylalanines followed by direct photocatalytic decarboxylative Giese cyclization. The SAR studies were conducted for the newly synthesized scaffolds to stimulate seed germination of Orobanche cumana. The trans-fused compounds showed better activity then the cis-fused compounds. However, the strigolactones 35/36 and 39/40 showed superior bioactivity than the GR245DS and GR244DO.(c) 2022 Elsevier Ltd. All rights reserved.