We described a novel stereoselective total synthesis of (-)-(6S,2'R)-cryptocaryalactone, a natural product containing syn/anti-6,8-diol/5,6-dihydro-2H-pyran-2-one unit. The approach, which characterised a highly diastereoselective chelation-controlled Mukaiyama aldol reaction of a benzyl-protected aldehyde and a Yamaguchi lactonisation of a δ-hydroxy-trans-α,β-unsaturated carboxylic acid, is an alternative synthetic strategy towards cryptocaryalactones.
Keywords: (–)-(6S,2′R)-cryptocaryalactone; Total synthesis; Yamaguchi lactonisation; chelation-controlled Mukaiyama aldol reaction; δ-hydroxy-trans-α,β-unsaturated carboxylic acid.