L-Phenyl-2-tetrazoline-5-thione

In a further exanple. Smith and Wan exploited the nucleophilic capability of l-phenyl-2-tetrazoline-5-thione in the Mitsunobu reaction, followed by oxidation to the sulfone with hydrogen peroxide and ammonium heptamolybdate tetrahydrate as a key step in a synthesis of the ansamycin antiobiotic, (+ )-thiazinotrienomycin-E (eq 8). Importantly, use of the phenyltetrazolylthione-derived sulfone gave an 13Z ratio of 10 1 in this coupling whereas the more conventional benzthiazole-2-thiol-derived system resulted in a selectivity of only 1.5 1 in favor of the -isomer. 

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