First Asymmetric Total Synthesis of (R,E)-1-[4-(3-Hydroxyprop-1-enyl)phenoxyl]-3-methylbutane-2,3-diol

Abstract

A new anti-inflammatory active phenylpropenoid, (R,E)-1-[4-(3-hydroxyprop-1-enyl) phenoxyl]-3-methylbutane-2,3-diol (1), isolated from the stem wood of Zanthoxylum integrifoliolum, has been synthesized for the first time using commercially available 4-hydroxy benzaldehyde (2). The key step involves the Sharpless asymmetric dihydroxylation of olefin (3).

Keywords:

• Phenylpropenoid
• (R,E)-1-[4-(3-hydroxyprop-1-enyl)phenoxyl]-3-methylbutane-2,3-diol
• sharpless asymmetric dihydroxylation

ACKNOWLEDGMENTS

The authors (V. S., K. R., and J. J. P. S.) are thankful to the University Grants Commission and the Council of Scientific and Industrial Research, New Delhi, India, for financial support and to Dr. J. S. Yadav, director, Indian Institute of Chemical Technology, for his encouragement.