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田泽酸B的首次全合成。

First Total Synthesis of Tanzawaic Acid B.

作者信息

Murata Takatsugu, Tsutsui Hisazumi, Yoshida Takumi, Kubota Hirokazu, Hiraishi Shintaro, Natsukawa Hiyo, Suzuki Yuki, Hiraga Daiki, Mori Takahiro, Maekawa Yutaro, Tateyama Satoru, Toyoyama Kiyotaka, Ito Keiichi, Suzuki Kyohei, Yonekura Keita, Shibata Natsumi, Sato Teruyuki, Tasaki Yasutaka, Inohana Takehiko, Takano Atsuhiro, Egashira Naoki, Honda Masaki, Umezaki Yuma, Shiina Isamu

机构信息

Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan.

出版信息

ACS Omega. 2023 Jul 19;8(30):27703-27709. doi: 10.1021/acsomega.3c03634. eCollection 2023 Aug 1.

Abstract

The first total synthesis of (+)-tanzawaic acid B, a natural polyketide bearing a pentadienoic ester and octalin moiety, has been accomplished. The synthetic improvement from previous synthetic conditions facilitated our gram-scale synthesis of the chiral octalin that possesses seven stereogenic centers and that is the core skeleton of almost all of the tanzawaic acid family.

摘要

(+)-檀泽酸B是一种带有戊二烯酸酯和八氢萘部分的天然聚酮化合物,其首次全合成已经完成。相对于之前的合成条件,合成方法的改进使我们能够以克级规模合成具有七个立体中心的手性八氢萘,该八氢萘是几乎所有檀泽酸家族化合物的核心骨架。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f875/10399178/5a5189398a0d/ao3c03634_0002.jpg

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