Total Syntheses of Phleghenrines A and C

• Type of Material: Article
• Authors: Xinpei Cai, Purdue University; Lei Li, Purdue University; Ye-Cheng Wang, Purdue University; Jianhan Zhou, Purdue University; Mingji Dai, Emory University
• Language: English
• Date: 2023-07-11
• Publisher: American Chemical Society
• Publication Version: Final Published Version
• Copyright Statement: © 2023 The Authors.
• License: Creative Commons Attribution 4.0 International
• Final Published Version (URL): http://dx.doi.org/10.1021/acs.orglett.3c01784
• Title of Journal or Parent Work: ORGANIC LETTERS
• Volume: 25
• Issue: 28
• Start Page: 5258
• End Page: 5261
• Keywords: LYCONADINS; Chemistry, Organic; EFFICIENT SYNTHESIS; Science & Technology; Physical Sciences; HUPERZINE; Chemistry; LYCOPODIUM ALKALOIDS; MASKED O-BENZOQUINONES
• Research Categories: Chemistry, Organic; Health Sciences, Oncology

Abstract

Herein, we report the total syntheses of phleghenrines A and C from commercially available starting materials in 7 and 8 steps, respectively. Notable steps include an inverse electron-demand Diels-Alder reaction between a masked o-benzoquinone and a N-protected enamine to prepare one key intermediate with a bicyclo[2.2.2]octenone core, a Büchner-Curtius-Schlotterbeck one-carbon insertion to expand the bicyclo[2.2.2]octenone to a bicyclo[3.2.2]nonenone, and Trauner’s modified 2-pyridone synthesis to install the 2-pyridone moiety.