Total Syntheses of Indole Terpenoids (−)-Lyngbyatoxin, (−)-Teleocidin A2, and (−)-7-Geranylindolactam V

IF 3.6 2区 化学 Q1 CHEMISTRY, ORGANIC Journal of Organic Chemistry Pub Date : 2025-01-01 DOI:10.1021/acs.joc.4c02877
Jordan MacQueen, Charles Wilber, Syed Faiq, Kelvin L. Billingsley
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Abstract

A regiodivergent palladium-catalyzed Suzuki–Miyaura reaction has been successfully implemented to synthesize (−)-lyngbyatoxin, (−)-teleocidin A2, and (−)-7-geranylindolactam V. This ligand-controlled cross-coupling strategy allowed for the direct preparation of these natural products from a single advanced synthetic intermediate, providing the shortest reported route to each compound. Subsequent in vitro studies in cancer cell lines were conducted to explore the chemotherapeutic applications of these natural products.

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吲哚萜类(−)- lyngybyatoxin,(−)-Teleocidin A2和(−)-7-Geranylindolactam V的全合成
区域发散钯催化的Suzuki-Miyaura反应已经成功地合成了(−)- lynynbyatoxin,(−)-teleocidin A2和(−)-7-geranylindolactam V.这种配体控制的交叉偶联策略允许从单个高级合成中间体直接制备这些天然产物,为每个化合物提供了报道的最短路线。随后在癌细胞系中进行了体外研究,以探索这些天然产物的化疗应用。
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来源期刊
Journal of Organic Chemistry
Journal of Organic Chemistry 化学-有机化学
CiteScore
6.20
自引率
11.10%
发文量
1467
审稿时长
2 months
期刊介绍: Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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