First Total Synthesis of Tanzawaic Acid B

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

doi:10.1021/acsomega.3c03634

First Total Synthesis of Tanzawaic Acid B

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

Authors

Takatsugu Murata¹, Hisazumi Tsutsui¹, Takumi Yoshida¹, Hirokazu Kubota¹, Shintaro Hiraishi¹, Hiyo Natsukawa¹, Yuki Suzuki¹, Daiki Hiraga¹, Takahiro Mori¹, Yutaro Maekawa¹, Satoru Tateyama¹, Kiyotaka Toyoyama¹, Keiichi Ito¹, Kyohei Suzuki¹, Keita Yonekura¹, Natsumi Shibata¹, Teruyuki Sato¹, Yasutaka Tasaki¹, Takehiko Inohana¹, Atsuhiro Takano¹, Naoki Egashira¹, Masaki Honda¹, Yuma Umezaki¹, Isamu Shiina¹

Affiliation

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

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.