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Paper | Special issue | Vol 93, No. 2, 2016, pp.647-672
Published online, 14th November, 2015
DOI: 10.3987/COM-15-S(T)52
A New Tactic for Tocopherol Synthesis Using Intramolecular Benzyne Trapping by an Alcohol

David W. Knight* and Qing Xu

*School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, U.K.

Abstract

A formal total synthesis of (S)-α-tocopherol, the major component of natural Vitamin E has been achieved using intramolecular benzyne trapping as a key step to form the chroman ring. The synthesis also features an efficient new method for benzotriazole N-amination using an oxaziridine; chiral, non-racemic intermediates are generated using asymmetric dihydroxylation.