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Further studies on the RuO 4 -catalyzed oxidative polycyclization of isoprenoid polyenes have been carried out. The configuration of the tris-THF product from the oxidation of geranylgeranyl acetate has been determined by a combination of spectral and chemical correlation methods. The oxidation of (E,Z)-farnesyl acetate, synthesized from nerol, has been carried out. This process stops at the...
Isoprenoid polyenes farnesyl acetate, geranylgeranyl acetate and squalene undergo oxidative polycyclization to bis-, tris-, and penta-tetrahydrofurane products, respectively, in the presence of catalytic amounts of RuO 4 (from RuO 2 ·2H 2 O) and NaIO 4 as primary oxidant. The stereochemistry of the bis-cyclization product was established as cis-threo-cis-threo through...
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