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)-alpha/beta/gamma/delta-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

A straightforward hetero Diels-Alder approach to (2-ambo, 4'R,8'R) alpha-, beta-, gamma- and delta-4-thiatocopherol / S. Menichetti; R. Amorati; M. G. Bartolozzi; G. F. Pedulli; A. Salvini; C. Viglianisi. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - .:(2010), pp. 2218-2225. [10.1002/ejoc.200901493]

A straightforward hetero Diels-Alder approach to (2-ambo, 4'R,8'R) alpha-, beta-, gamma- and delta-4-thiatocopherol

MENICHETTI, STEFANO
;
SALVINI, ANTONELLA;VIGLIANISI, CATERINA
2010

Abstract

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)-alpha/beta/gamma/delta-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
2010
.
2218
2225
S. Menichetti; R. Amorati; M. G. Bartolozzi; G. F. Pedulli; A. Salvini; C. Viglianisi
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/386211
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