Approaches to analogues of anhydrogliotoxin IV Syntheses and reactions of 2‐mercapto‐2‐aminopropionic acid derivatives

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Abstract
Several S,N‐protected‐2‐mercapto‐2‐aminopropionic acid derivatives (3a‐g Table I) have been prepared by the reaction of thiols with the corresponding N‐protected 2‐hydroxy‐2‐amino‐propionic acid derivatives 8, prepared from the corresponding amides 7 and pyruvic acid. Recent controversies in the literature regarding this method are discussed. Selective removal of the sulfur‐protecting group in 3b and 3e afforded the 2‐mercapto‐2‐acylamidopropionic acids 11, R2 = H and C6H5 respectively. Reaction of 3e with thionyl chloride afforded 4‐methyl‐4‐(acetylthio)‐2‐phenyl‐2‐oxazolin‐5‐one 10. Under these conditions 3g gave the Leuchs' anhydride 14.