Concise Synthesis of (S)-δ-CEHC, a Metabolite of Vitamin E.

作者: Guangrong Zheng , Peiyi Zhang , Pratik Pal , Xuan Zhang , Matthew Burke

DOI: 10.1021/ACSOMEGA.0C05658

关键词: Yield (chemistry)MetaboliteStereochemistrySynthonVitamin EChemistryTotal synthesisUrinary levels

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

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