Synthesis and absolute configuration of natural 8-hydroxyl-9-angeloyloxythymol

ABSTRACT

8-Hydroxyl-9-angeloyloxythymol, isolated from Eupatorium fortuneri Turcz, was synthesized for the first time. The synthesis was achieved through a seven-step route, using m-cresol as the starting material and Sharpless asymmetric dihydroxylation to install the quaternary stereogenic center. The enantio-enriched synthetic sample showed spectroscopic data consistent with those of the natural product and thus confirmed the gross structure assigned previously. By comparing the sign for optical rotations of the synthetic and the natural samples, the absolute configuration for the natural product was also assigned.

GRAPHICAL ABSTRACT

KEYWORDS:

• Asymmetric dihydroxylation
• natural product
• quaternary stereogenic centers
• stereochemistry
• thymol derivative

Acknowledgments

The research is supported by Jiangsu University (No. 14JDG018) and the Priority Academic Program Development of Jiangsu Higher Education Institutions.