The synthetic potentialities of cerium(III) chloride are demonstrated by the synthesis of a nine-membered ring heterocycle component of Griseoviridin (3) in optically active form. The key step involves the stereospecific formation of the α-carbalkoxy alkenyl sulfide moiety using a combination system of cerium(III) chloride heptahydrate and sodium iodide.
A Novel Route to the Vinyl Sulfide Nine-Membered Macrocycle Moiety of Griseoviridin† / E. Marcantoni, M. Massaccesi, M. Petrini, G. Bartoli, M.C. Bellucci, M. Bosco, L. Sambri. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 65:15(2000), pp. 4553-4559. [10.1021/jo000116d]
A Novel Route to the Vinyl Sulfide Nine-Membered Macrocycle Moiety of Griseoviridin†
M.C. Bellucci;
2000
Abstract
The synthetic potentialities of cerium(III) chloride are demonstrated by the synthesis of a nine-membered ring heterocycle component of Griseoviridin (3) in optically active form. The key step involves the stereospecific formation of the α-carbalkoxy alkenyl sulfide moiety using a combination system of cerium(III) chloride heptahydrate and sodium iodide.
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