Abstract
The adducts of 3,4-epoxyprecocene II (1b) with N-acetyl-L-cysteine, L-cysteine, and glutathione (GSH), in which a formal syn addition of the thiol reagent to the oxirane has taken place, with the sulfur atom linked to the benzylic position of the benzopyranyl skeleton of 1b, have been synthesized. A stereochemical correlation between the two sets of diastereomeric cis adducts 3, 5, and 6 formed, i.e. the 3R,4S and 3S,4R series, has been established by spectroscopic, chromatographic, and enzymatic means
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