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… Click to show full abstract
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)-δ-CEHC was accomplished in 40% overall yield and 97% ee using a chiral synthon derived from naturally occurring (−)-linalool.
               
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