1227952-60-4Relevant articles and documents
A straightforward hetero-diels-alder approach to (2-ambo,4′R, 8′R)-α/β/γ/δ-4-thiatocopherol
Menichetti, Stefano,Amorati, Riccardo,Bartolozzi, Maria Grazia,Pedulli, Gian Franco,Salvini, Antonella,Viglianisi, Caterina
, p. 2218 - 2225 (2010)
A simple and original inverse electron demand hetero-Diels-Alder reaction has been successfully applied to the synthesis of (2-ambo,4′R,8′R)- α/β/γ/δ-4-thiatocopherol. Commercially available methyl hydroquinones and. (2E,7R,11R)-(+)-phytol were exploited for the preparation of the ortho-thioquinones, acting as electron-poor dienes, and of the proper 1,3-diene used as dienophile, respectively. The benzoxathiine cycloadducts, with the required tocopherol-like skeleton, were obtained with complete control, of regio and chemoselectivity. The antioxidant activity of 4-thiatocopherols was measured and rationalized in comparison with that of the corresponding natural components of Vitamin E.
