Asymmetric Synthesis of Rugulotrosin A

Jianhua Chen; Yayue Li; Zheming Xiao; Haibing He; Shuanhu Gao

doi:10.1021/acs.orglett.0c00063

Asymmetric Synthesis of Rugulotrosin A

Org Lett. 2020 Feb 21;22(4):1485-1489. doi: 10.1021/acs.orglett.0c00063. Epub 2020 Feb 10.

Authors

Jianhua Chen¹, Yayue Li¹, Zheming Xiao¹, Haibing He², Shuanhu Gao^{1

2}

Affiliations

¹ Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering , East China Normal University , 3663 North Zhongshan Road , Shanghai 200062 , China.
² Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development , East China Normal University , 3663 North Zhongshan Road , Shanghai 200062 , China.

PMID: 32037839
DOI: 10.1021/acs.orglett.0c00063

Abstract

A new approach was developed to construct the tetrahydroxanthone by a Knoevenagel condensation/6π-electronic cyclization/aromatization cascade starting from readily available cyclohexane-1,3-diones and unsaturated aldehydes. This strategy provides a new solution for the preparation of monomeric tetrahydroxanthones bearing different functional groups at C-12. As a synthetic application, the asymmetric formal synthesis of rugulotrosin A was achieved.