Asymmetric Total Synthesis of Cerorubenic Acid-III

Xin Liu; Junyang Liu; Jianlei Wu; Guocheng Huang; Rong Liang; Lung Wa Chung; Chuang-Chuang Li

doi:10.1021/jacs.8b12647

Asymmetric Total Synthesis of Cerorubenic Acid-III

J Am Chem Soc. 2019 Feb 20;141(7):2872-2877. doi: 10.1021/jacs.8b12647. Epub 2019 Feb 7.

Authors

Xin Liu^{1

2}, Junyang Liu^{1

3}, Jianlei Wu¹, Guocheng Huang¹, Rong Liang¹, Lung Wa Chung¹, Chuang-Chuang Li¹

Affiliations

¹ Shenzhen Grubbs Institute, Department of Chemistry , Southern University of Science and Technology , Shenzhen 518055 , China.
² Institute of Chinese Medical Sciences , University of Macau , Macau , China.
³ Academy for Advanced Interdisciplinary Studies , Southern University of Science and Technology (SUSTech) , Shenzhen 518055 , China.

PMID: 30721058
DOI: 10.1021/jacs.8b12647

Abstract

The first asymmetric total synthesis of the highly strained compound cerorubenic acid-III is reported. A type II intramolecular [5 + 2] cycloaddition allowed efficient and diastereoselective construction of the synthetically challenging bicyclo[4.4.1] ring system with a strained bridgehead (anti-Bredt) double bond in the final product. A unique transannular cyclization installed the vinylcyclopropane moiety with retention of the desired stereochemistry.

Publication types

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