Asymmetric Total Synthesis of (-)-Spirochensilide A

Xin-Ting Liang; Jia-Hua Chen; Zhen Yang

doi:10.1021/jacs.0c02522

Asymmetric Total Synthesis of (-)-Spirochensilide A

J Am Chem Soc. 2020 May 6;142(18):8116-8121. doi: 10.1021/jacs.0c02522. Epub 2020 Apr 20.

Authors

Xin-Ting Liang¹, Jia-Hua Chen¹, Zhen Yang^{1

2

3}

Affiliations

¹ Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science, and Peking-Tsinghua Center for Life Sciences, Peking University, Beijing, 100871, China.
² State Key Laboratory of Chemical Oncogenomics and Key Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen 518055, China.
³ Shenzhen Wan Laboratory, Shenzhen, 518055, China.

PMID: 32286815
DOI: 10.1021/jacs.0c02522

Abstract

An asymmetric total synthesis of (-)-spirochensilide A has been achieved for the first time. The synthesis features a semipinacol rearrangement reaction to stereoselectively construct the two-vicinal quaternary chiral centers at C8 and C10, a tungsten-mediated cyclopropene-based Pauson-Khand reaction to install the C13 quaternary chiral center, and a furan-based oxidative cyclization to stereoselectively form the spiroketal motif.

Publication types

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