从 OUPS-N133 中分离得到的 Peribysin 天然产物的结构翻转：Peribysin A、B、C、F 和 G 的合成及立体化学修订。
Overturning the Peribysin Family Natural Products Isolated from OUPS-N133: Synthesis and Stereochemical Revision of Peribysins A, B, C, F, and G.
机构信息
Organic Chemistry Division, CSIR-National Chemical Laboratory, Pune 411008, India.
Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India.
出版信息
Org Lett. 2020 Apr 17;22(8):3104-3109. doi: 10.1021/acs.orglett.0c00857. Epub 2020 Apr 7.
Herein we report the stereochemical revision of peribysins A, B, C, F, and G, guided by enantiospecific total synthesis starting from (+)-nootkatone. Furthermore, we reconfirmed the absolute stereochemistry of peribysin Q. The highlights of the synthesis are enone transposition and kinetic iodination resulting in separation of diastereomers. Our findings coupled with synthetic and biological data previously reported by Danishefsky's group suggest that the original stereochemistries of peribysins A, B, C, F, and G were misassigned.
在这里，我们报告了 peribysins A、B、C、F 和 G 的立体化学修订，该修订由从 (+)-nootkatone 开始的对映体特异性全合成指导。此外，我们重新确认了 peribysin Q 的绝对立体化学。该合成的重点是烯酮的反式移位和动力学碘化，导致非对映异构体的分离。我们的发现以及 Danishefsky 小组之前报道的合成和生物学数据表明，peribysins A、B、C、F 和 G 的原始立体化学结构被错误指定。
Zotero 插件