ChemInform Abstract: Thiotropocin Biosynthesis. Shikimate Origin of a Sulfur-Containing Tropolone Derivative

Feeding of [U- 13 C 6 ]glucose to Pseudomonas CB-104 gave labeled thiotropocin (1a and 1b). The 13 C NMR spectrum of the derived p-bromobenzyl thioether (2a and 2b) displayed a pattern of enhancements and couplings consistent with a shikimate origin for thiotropocin by way of a symmetrical phenylpyruvate (11) intermediate. The latter metabolite is proposed to undergo oxidative ring expansion followed by further oxidation and oxygen-sulfur exchange