Calixanthomycin A: Asymmetric Total Synthesis and Structural Determination

Kuanwei Chen; Tao Xie; Yanfang Shen; Haibing He; Xiaoli Zhao; Shuanhu Gao

doi:10.1021/acs.orglett.1c00193

Calixanthomycin A: Asymmetric Total Synthesis and Structural Determination

Org Lett. 2021 Mar 5;23(5):1769-1774. doi: 10.1021/acs.orglett.1c00193. Epub 2021 Feb 19.

Authors

Kuanwei Chen¹, Tao Xie¹, Yanfang Shen¹, Haibing He², Xiaoli Zhao¹, 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: 33605734
DOI: 10.1021/acs.orglett.1c00193

Abstract

We report the first asymmetric total synthesis and structural determination of calixanthomycin A. Taking advantage of a modular strategy, a concise approach was developed to assemble the hexacyclic skeleton with both enantiomers of the lactone A ring. Stereoselective glycosylation coupled the angular hexacyclic framework with a monosaccharide fragment to produce calixanthomycin A and its stereoisomers. This enable us to determine and assign the absolute configuration of C-25 (25S) and monosaccharide (derivative of l-glucose).

Publication types

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

MeSH terms

Glycosylation
Lactones / chemistry*
Molecular Structure
Monosaccharides / chemical synthesis*
Monosaccharides / chemistry
Stereoisomerism

Substances

Lactones
Monosaccharides