Stereoselective Total Synthesis of (±)-5- epi-Cyanthiwigin I via an Intramolecular Pauson-Khand Reaction as the Key Step

Yuanyuan Chang; Linlin Shi; Jun Huang; Lili Shi; Zichun Zhang; Hong-Dong Hao; Jianxian Gong; Zhen Yang

doi:10.1021/acs.orglett.8b00903

Stereoselective Total Synthesis of (±)-5- epi-Cyanthiwigin I via an Intramolecular Pauson-Khand Reaction as the Key Step

Org Lett. 2018 May 18;20(10):2876-2879. doi: 10.1021/acs.orglett.8b00903. Epub 2018 May 9.

Authors

Yuanyuan Chang¹, Linlin Shi¹, Jun Huang¹, Lili Shi¹, Zichun Zhang¹, Hong-Dong Hao¹, Jianxian Gong¹, Zhen Yang^{1

2

3}

Affiliations

¹ State Key Laboratory of Chemical Oncogenomics, Key Laboratory of Chemical Genomics , Peking University Shenzhen Graduate School , Shenzhen 518055 , China.
² Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), and Peking-Tsinghua Center for Life Sciences , Peking University , Beijing 100871 , China.
³ Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy , Ocean University of China , 5 Yushan Road , Qingdao 266071 , China.

PMID: 29741093
DOI: 10.1021/acs.orglett.8b00903

Abstract

A convenient approach to the construction of the 5-6-7 tricarbocyclic fused core structure of cyanthiwigins via a Co-mediated Pauson-Khand reaction as a key step has been developed. The cyathane core intermediate obtained by this strategy was used in the concise synthesis of (±)-5- epi-cyanthiwigin I. The developed chemistry paves the way for the total synthesis of structurally diverse cyanthiwigins.

Publication types

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