Journal of Organic Chemistry p. 5803 - 5809 (1994)
Update date:2022-08-04
Topics:
Zheng, Yi Feng
Oehlschlager, Allan C.
Hartman, Peter G.
Synthesis of (6E)-8-thia-2,3-oxidosqualene (22) and (14E)-13-thia-2,3-oxidosqualene (34) as inhibitors of 2,3-oxidosqualene-lanosterol cyclase are reported.Synthesis of 22 required the stereospecific generation of a vinyl sulfide.This was achieved by a new coupling of a benzenethiosulfonate (15) and a lithiated vinyl iodide (18).Synthesis of 34 involved similar coupling of benzenethiosulfonate 29 with lithium reagent obtained from vinyl iodide 33.The required (E)-vinyl iodides 18 and 33 were prepared by zirconium-catalyzed carboalumination of 4-pentyn-1-ol, (16) and 2,6-dimethyl-2(E),6(E)-dien-10-yne (32) respectively.Both 22 and 34 inhibited 2,3-oxidosqualene-lanosterol cyclase from Candida albicans with IC 50 values of 0.68 and 45 μM, respectively.
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