Concise Synthesis Of (S)-Delta-Cehc, A Metabolite Of Vitamin E

Carboxyethyl hydroxychromans (CEHCs) are natural metabolites of vitamin E (VE). Their urinary levels can serve as useful biomarkers for the nutritional assessment of VE. Moreover, specific biological activities of CEHCs deserve further investigation. Here, we report a concise method to build up a chiral 6-hydroxychroman scaffold of VE and CEHCs. The first total synthesis of (S)-delta-CEHC was accomplished in 40% overall yield and 97% ee using a chiral synthon derived from naturally occurring (-)-linalool.