Lanosterol (59)

FIGURE 2-15 Proposed mechanism for the cyclization of 2,3-oxidosqualene (57) to produce lanosterol (59). This mechanism is postulated from model organic reactions.

biosynthesis of cholesterol, particularly in hypercholesterolemia, a familial disorder of lipid metabolism.

Sodium 2-phenylbutyrate (62) and sodium (p-chloro-phenox)isobutyrate (or Clofibrate) (63) are both aryl-substituted short chain fatty acids that interfere with the acylation of coenzyme A and block the initiation of cholesterol synthesis. Benzmalacene (64) blocks sterol synthesis somewhere between isopentenyl pyrophosphate and farnesyl pyrophosphate. Analogs of tris[2-

(diethylamino)ethyl]phosphate trihydrochloride, such as SKF-7997 (65), effectively block the cyclization of the 2,3-epoxide of squalene. Both MER-29 (66) and 22,25-diazacholestanol (67) block the reduction of desmosterol to cholesterol, while AY-9944 (68) blocks the conversion of 7-dehydrocholesterol to cholesterol. Lovastatin (69) has been approved by the FDA for use as a serum cholesterol-lowering agent; it acts as an inhibitor of HMG-CoA reductase.

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