We describe the versatile and concise total synthesis of all stereoisomers of tarchonanthuslactone from (R)- or (S)-3-hydroxybutyrate via eight steps. The key steps of the synthesis include a highly diastereoselective chelation-controlled Mukaiyama aldol reaction of a p-methoxybenzyl-protected aldehyde and a Yamaguchi lactonization of a δ-hydroxy-trans-α,β-unsaturated carboxylic acid.
Key words
total synthesis - tarchonanthuslactone - chelation-controlled Mukaiyama aldol reaction - δ-hydroxy-
trans-α,β-unsaturated carboxylic acid - Yamaguchi lactonization