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Semi-synthesis of 5- and 7-formyltocopherols and tocotrienols has been developed by ortho-formylation of C-5 or C-7-unsubstituted vitamin E derivatives (14 examples) up to 90% yield, through heating in the presence… Click to show full abstract
Semi-synthesis of 5- and 7-formyltocopherols and tocotrienols has been developed by ortho-formylation of C-5 or C-7-unsubstituted vitamin E derivatives (14 examples) up to 90% yield, through heating in the presence of respectively 10-10-15 equivalents of MgCl2-Et3N-(CH2O)n. Formylation of 5-bromo-δ-tocotrienol revealed an unprecedented 5-bromo/7-formyl exchange and yielded 7-bromo-5-formyl-δ-tocotrienol as major product. The minor 5-bromo-7-formyl-δ-tocotrienol led in three steps to 7-formyl-δ-tocotrienol previously isolated from the stem bark of Garcinia virgata.
Journal Title: Tetrahedron
Year Published: 2017
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