Reductomycin

The other group of unsaturated amides derived from 2-amino-3-hydroxycyclopenten-2-one is composed of reductomycin (59), reductline, (60), limocrocin (61) and the enopeptins A (62) and B (63). 

The synthesis of reductomycin (59) [120] has been carried out starting from 3-(hydroxy-methyl)furan, which was oxidized with lead(IV) acetate to the corresponding 2,5-diacetoxy derivative. Subsequent hydrogenation of the double bond and oxidation afforded the appropriate aldehyde. A Wittig reaction of this compound and deprotection of the trichloroethyl ester followed by esterification with 3-hydroxy-2-nitrosocyclopent-2-en-1-one gave an ester, which was then reduced with zinc. Reductomycin (59) was obtained after intramolecular O—> N acyl migration (Scheme 33). 

As with reductomycin (59), reductiline (60) has been isolated from the fermentation broth of a variant of Streptomyces orientalis [122]. Its structure is related to reductomycin (59), the difference being that the acetoxydihydrofuran unit has been substituted by the N-(3-methylthiopropyl)pyrrole. Biogenetically, reductiline (60) could be considered to originate from reductiomycin (59) and methionine. The synthesis of reductiline (60) has been carried out from formylated (1-cyanopropanal dimethylacetal. After condensation of this aldehyde with... 

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