110211-08-0Relevant articles and documents
Total synthesis of leustroducsin B
Shimada, Kousei,Kaburagi, Yosuke,Fukuyama, Tohru
, p. 4048 - 4049 (2007/10/03)
A convergent total synthesis of leustroducsin B (1), which is known to exhibit a variety of biological activities, was successfully carried out. Notable features of our synthesis include construction of the C8 stereocenter by lipase-mediated desymmetrizat
Regioselective Synthesis of Hydroxy Sulphides via Trifluoroacetoxysulphenylation of Derivatives of Allylic Alcohols
Samii, Zakaria K. M. Abd El,Ashmawy, Mohamed I. Al,Mellor, John M.
, p. 2509 - 2516 (2007/10/02)
Reaction of manganese(III) acetate with diphenyl disulphide in dichloromethane-trifluoroacetic acid in the presence of allylic esters gives trifluoroacetoxy sulphides, which on hydrolysis readily afford vicinal hydroxy sulphides.With acetate esters, neighbouring group participation by the acetate functionality controls the reaction course.Thus regiospecific addition to allyl acetate affords after hydrolysis only 3-phenylthiopropane-1,2-diol.In contrast, with trifluoroacetate esters the inductive effects of the trifluoroacetate functionality lead to a different regiocontrol.Thus addition of diphenyl disulphide to allyl trifluoroacetate gives after hydrolysis only 2-phenylthiopropane-1,3-diol.The regio- and stereochemistry of addition to a variety of other allylic (and homoallylic) esters is described and the extension of this type of regiocontrol is discussed.
REGIOSELECIVE HYDROXYSULPHENYLATION OF DERIVATIVES OF ALLYLIC ALCOHOLS AND AMINES
Samii, Zakaria K M Abd El,Ashmawy, Mohamed I Al,Mellor, John M
, p. 5289 - 5292 (2007/10/02)
Reaction of manganic acetate with diphenyldisulphide in dichloromethane-trifluoroacetic acid in the presence of allylic esters or amides of allylamine gives trifluoroacetoxysulphides and hence by ready hydrolysis vicinal hydroxysulphides.The regiochemical outcome can be controlled by selection of either an acetyl- or trifluoroacetyl derivative.
