Two key reaction types were used for the total synthesis of the antibiotic agent (+)‐TMC‐151C: the vinylogous Mukaiyama aldol reaction and silicon‐tethered ring‐closing metathesis (RCM; see scheme). This strategy should provide efficient access to a range of related natural polyketides containing pent‐2‐ene‐1,5‐diol units.

Scheme 1. Strategy for pent-2-ene-1,5-diol unit by silicon-tethered ringclosing metathesis.Scheme 2. Unusual E-selective RCM to form the eight-membered-ring compound 2 a. Reagents and conditions: a) HG-II (20 mol %), para-benzoquinone (1.5 equiv)/ xylene, reflux, 24 h. The diastereomeric ratio was determined by 1 H NMR analysis. HG-II = Hoveyda-Grubbs second-generation catalyst.

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Two key reaction types were used for the total synthesis of the antibiotic agent (+)‐TMC‐151C: the vinylogous Mukaiyama aldol reaction and silicon‐tethered ring‐closing metathesis (RCM; see scheme). This strategy should provide efficient access to a range of related natural polyketides containing pent‐2‐ene‐1,5‐diol units.

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