Total synthesis of kehokorins A and B. Issue 18 (2nd May 2019)

• Record Type: Journal Article
• Authors: Fujiwara, Kenshu; Motousu, Ryosuke; Sato, Daisuke; Kondo, Yoshihiko; Akiba, Uichi; Suzuki, Takanori; Tokiwano, Tetsuo
• Is Part Of: Tetrahedron letters. Volume 60:Issue 18(2019)
• Page Start: 1299
• Page End: 1301
• Publication Date: 2019-05-02
• Subjects: Natural product synthesis -- Cytotoxin -- Dibenzofuran rhamnoside -- p-Terphenyl; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.04.011
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Successful total synthesis of kehokorins A and B. A strategy based on dibenzofuran formation followed by p -terphenyl construction. Construction of the dibenzofuran unit by Suzuki coupling and Ullmann ether synthesis. 7-Bromodibenzofuran formation via dibromination of the core followed by debromination. Abstract: The total synthesis of a dibenzofuran rhamnoside, kehokorin A, and its aglycone, kehokorin B, was achieved via a route including Suzuki-Miyaura cross-coupling followed by Ullmann ether synthesis to form a dibenzofuran, stepwise bromination at C7 of the dibenzofuran, a second Suzuki-Miyaura cross-coupling to install a 4-methoxyphenyl group at C7, and rhamnosylation.