Tetrahedron p. 1179 - 1182 (1980)
Update date:2022-08-03
Topics:
Welch, Steven C.
Gruber, John M.
Rao, Prakasa A. S. C.
Epoxidation of retinol (vitamin A alcohol, 1) with freshly prepared and standardized mono-perphtalic acid in ether affords a product which Karrer named "chromogen 574" in 1945.Repetition of this peracid oxidation of retinol (1) with several peracids (m-PPA, m-CPBA, or CH3CO3H) with or without a buffer (NaHCO3 or Na2HPO4) produces dihydropyran alcohol 4 as characterised by spectroscopy and subsequent chemical transformations.Thus the structures proposed for "chromogen 574" by Karrer in 1945-47 and Troitskii in 1948 are now revised to correspond to cyclic alkohol 4.
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(1967)Doi:10.1021/ja040065s
(2004)Doi:10.1021/jo00111a044
(1995)Doi:10.1016/S0031-9422(00)86148-8
(1965)Doi:10.1039/c3cc49313j
(2014)Doi:10.1016/0040-4039(80)80197-3
(1980)
