Wild-fire toxin

Widman-Stoermer synthesis, 3, 43 Wild-fire toxin, 7, 249 Willardiine,... 

Widman-Stoermer synthesis, 3, 43 Wild-fire toxin, 7, 249 Willardiine, synthesis, 3, 146 Willgerodt reaction thiophene synthesis by, 4, 883 Williamson reaction oxetane synthesis by, 7, 390-391 Withasomnine occurrence, 5, 302 Wittig reaction crown ethers and, 7, 759 Wittig-Homer reactions crown ethers and, 7, 759 Wolff rearrangement oxirenes in, 7, 120, 126... 

VIII. Pachystermines, Wild-Fire Toxin and Antimetabolites. 49... 

Wild-fire toxin is produced by Pseudomonas tabaci, an organism which causes a leafspot disease in tobacco plants. The correct structure was determined by Stewart (2), and shown to be (241), although no assignment of stereochemistry was made. Wild-fire toxin is an unstable substance rapidly converted at neutral pH to isotabtoxin (242) by way of intramolecular attack of the amino-group on the 3-lactam. Hydrolysis of wildfire toxin gives threonine and tabtoxinine (243). 

In the course of a screening programme which produced a number of antimetabolites from various microorganisms, Scannell has described the isolation of a monocyclic P-lactam from an unidentified Streptomyces species (i). The compound was identified as (244), and is somewhat similar to the wild-fire toxin. 

A stereospecific synthesis of the wild-fire toxin (tabtoxin) has recently been described (2/9). 

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