Total Synthesis of (-)-Retigeranic Acid A: A Reductive Skeletal Rearrangement Strategy

Dongyu Sun; Ruyi Chen; Dongmin Tang; Qidong Xia; Yifan Zhao; Chun-Hui Liu; Hanfeng Ding

doi:10.1021/jacs.3c03178

Total Synthesis of (-)-Retigeranic Acid A: A Reductive Skeletal Rearrangement Strategy

J Am Chem Soc. 2023 Jun 7;145(22):11927-11932. doi: 10.1021/jacs.3c03178. Epub 2023 May 24.

Authors

Dongyu Sun¹, Ruyi Chen¹, Dongmin Tang¹, Qidong Xia², Yifan Zhao¹, Chun-Hui Liu¹, Hanfeng Ding¹

Affiliations

¹ Department of Chemistry, Zhejiang University, Hangzhou 310058, China.
² College of Chemistry, Jilin University, Changchun 130012, China.

PMID: 37224289
DOI: 10.1021/jacs.3c03178

Abstract

The asymmetric total synthesis of (-)-retigeranic acid A was described, which relies on a crucial reductive skeletal rearrangement cascade for the controllable assembly of diverse angular triquinane subunits. Taken together with an intramolecular Michael/aldol cyclization, an ODI-[5 + 2] cycloaddition/pinacol rearrangement cascade, a Wolff ring contraction and a stereoselective HAT reduction, our synthetic approach has enabled the access to (-)-retigeranic acid A in a concise and practical manner.