Total synthesis of xiamenmycin C and all of its stereoisomers: stereochemical revision

Yang-Yang Yao; Xiao-Yu Liu; Xiao-Yu Li; Hong-Guang Yang; Li Li; Xiao-Zhen Jiao; Ping Xie

doi:10.1080/10286020.2016.1188808

Total synthesis of xiamenmycin C and all of its stereoisomers: stereochemical revision

J Asian Nat Prod Res. 2016 Oct;18(10):976-87. doi: 10.1080/10286020.2016.1188808. Epub 2016 Jun 3.

Authors

Yang-Yang Yao¹, Xiao-Yu Liu¹, Xiao-Yu Li¹, Hong-Guang Yang¹, Li Li¹, Xiao-Zhen Jiao¹, Ping Xie¹

Affiliation

¹ a State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Beijing Key Laboratory of Active Substance Discovery and Druggability Evaluation , Institute of Materia Medica, Chinese Academy of Medical Science & Pecking Union Medical College , Beijing 100050 , China.

PMID: 27256638
DOI: 10.1080/10286020.2016.1188808

Abstract

Xiamenmycin C, a potent anti-fibrotic natural product, and all of its stereoisomers have been synthesized and their structures were fully characterized. Based on this study, the originally proposed structure of xiamenmycin C has been accordingly revised to be 2R,3S.

Keywords: Xiamenmycin C; stereochemical revision; total synthesis.

MeSH terms

Benzopyrans / chemical synthesis*
Benzopyrans / chemistry
Biological Products / chemical synthesis*
Biological Products / chemistry
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Stereoisomerism
Threonine / analogs & derivatives*
Threonine / chemical synthesis
Threonine / chemistry

Substances

Benzopyrans
Biological Products
N-((3,4-dihydro-3-hydroxy-2-methyl-2-(4'-methyl-3'-pentenyl)-2H-1-benzopyran-6-yl)carbonyl)threonine
Threonine