Enantioselective total synthesis of β-zearalenol from (s)-propylene oxide

ABSTRACT

The total synthesis of 14-membered resorcylic acid macrolide, β-zearalenol, was accomplished starting from commercially available enantiomerically pure propylene oxide and methyl 2,4-dihydroxy-6-methylbenzoate using Grignard reaction, asymmetric dihydroxylation, Yamaguchi macrolactonization, and ring-closing metathesis as key steps.

GRAPHICAL ABSTRACT

KEYWORDS:

• β-Zearalenol
• Grignard reaction
• Grubbs RCM
• S-propylene oxide
• Yamaguchi macrolactonization

Acknowledgments

The authors are thankful to GVK Bio Sciences and CSIR, New Delhi for constant encouragement in providing laboratory facilities and analytical data.

Additional information

Funding

This work was supported by the Council for Scientific and Industrial Research [CSC0114].