塔格糖毒素的全合成。
Total Synthesis of Tagetitoxin.
机构信息
Department of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
出版信息
J Am Chem Soc. 2020 Aug 12;142(32):13683-13688. doi: 10.1021/jacs.0c06641. Epub 2020 Jul 27.
Abstract
The intriguing structure of tagetitoxin (), a long-standing challenge in natural product synthesis, has been the subject of multiple revisions and has been confirmed through total synthesis. The route commences from a renewable furan starting material and features a number of unusual transformations (such as rearrangements, bromocyclization, and P(V)-based phosphate installation) to arrive at the target in 15 steps. As the route was designed to enable access to both enantiomers, the absolute configuration of the natural product could be assigned using a bioassay on (+)- and (-)-.
摘要
猫眼草毒素 () 的结构非常有趣，这是天然产物合成中长期存在的挑战，已经经过多次修订，并通过全合成得到了证实。该路线从可再生的呋喃起始原料开始，具有许多不寻常的转化（如重排、溴环化和基于 P(V) 的磷酸酯安装），最终在 15 步反应中得到目标产物。由于该路线的设计旨在使两种对映异构体都能够获得，因此可以使用 (+)-和 (-)-对映体的生物测定来确定天然产物的绝对构型。
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