Total synthesis of pyranicin was achieved using Cl2Pd(CH3CN)2-catalyzed diastereoselective cyclization of the allylic ester as the key step. The inhibitory activity of this compound for mitochondrial NADH-ubiquinone oxidoreductase (complex I) was slightly poorer than that of ordinary mono-THF acetogenins such as cis-solamin.
Total synthesis of pyranicin and its deoxygenated analogues were achieved using Cl 2 Pd(CH 3 CN) 2 catalyzed diastereoselective cyclization of the allylic ester as the key step. The inhibitory activity of these compound for mitochondrial NADH-ubiquinone oxidoreductase (complex I) was poorer than those of ordinary mono-THF acetogenins such as annonacin.
The first synthesis of (+)- and (-)-akolactone A is described by using Pd-catalyzed carbonylation. A comparison of the optical rotation of both enantiomers of akolactone A and the natural compound suggests that the absolute configuration at the 4-position of akolactone A is R.
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