Stereoselective synthesis of 5′-hydroxyzearalenone.

Graphical abstract Highlights • First total synthesis of 14 membered 5′-hydroxyzearalenone has been achieved. • Starting material used are easily available 1,4-butane diol and propylene oxide. • Two chiral centers are created using well established protocols (Sharpless, Jocobsen). • Synthesis was achieved in 18 longest linear sequence with an overall yield of 3.6%. Abstract A first stereoselective total synthesis of 14-memebered β-resorcylic macrolactone 5′-hydroxyzearalenone (1) has been achieved. The key steps are Jocobsen hydrolytic kinetic resolution, Sharpless asymmetric dihydroxylation, Vilsmeier-Haack reaction, Mitsunobu esterification and ring-closing metathesis. [ABSTRACT FROM AUTHOR]