First Total Syntheses of Tetracenomycins C and X

Shogo Sato; Keiichiro Sakata; Yoshimitsu Hashimoto; Hiroshi Takikawa; Keisuke Suzuki

doi:10.1002/anie.201707099

First Total Syntheses of Tetracenomycins C and X

Angew Chem Int Ed Engl. 2017 Oct 2;56(41):12608-12613. doi: 10.1002/anie.201707099. Epub 2017 Aug 30.

Authors

Shogo Sato¹, Keiichiro Sakata¹, Yoshimitsu Hashimoto^{1

2}, Hiroshi Takikawa^{1

3}, Keisuke Suzuki¹

Affiliations

¹ Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo, 152-8551, Japan.
² Present address: Showa Pharmaceutical University, 3-3165 Higashi-Tamagawagakuen, Machida, Tokyo, 194-8543, Japan.
³ Present address: Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto, 606-8501, Japan.

PMID: 28762249
DOI: 10.1002/anie.201707099

Abstract

The first total syntheses of tetracenomycins C and X were achieved, featuring 1) preparation of a hexasubstituted naphthonitrile oxide by successive benzyne cycloadditions and an oxidative ring-opening reaction; 2) a novel ortho-quinone mono-acetal as the A-ring unit; 3) construction of three contiguous stereogenic centers by an asymmetric benzoin cyclization, an isoxazole oxidation, and a stereoselective reduction.

Keywords: antibiotics; asymmetric synthesis; benzyne; isoxazoles; nitrile oxide.

Publication types

Research Support, Non-U.S. Gov't