Browsing Chemistry by Author "Baidilov, Daler"
Chemoenzymatic Approach to Tetrodotoxin: Synthesis of Fukuyama’s, Alonso’s, and Sato’s Advanced IntermediatesBaidilov, Daler; Rycek, Lukas; Trant, John F.; Froese, Jordan; Murphy, Brennan; Hudlicky, Tomas (Wiley, 2018-05-11)The advanced intermediates in the syntheses of tetrodotoxin reported by Fukuyama, Alonso, and Sato were prepared. The key steps in the synthesis of the title compounds involved the toluene dioxygenase–mediated dihydroxylation of either iodobenzene or benzyl acetate. The resulting diene diols were transformed to Fukuyama’s intermediate in six steps, to Alonso’s intermediate in nine steps and to Sato’s intermediate in ten steps, respectively.
Chemoenzymatic Synthesis of the Antifungal Compound(–)-Pestynol by a Convergent, Sonogashira Construction of the Central Yne-DieneBorra, Suresh; Kumar, Manoj; McNulty, James; Baidilov, Daler; Hudlicky, Tomas (Wiley, 2018-10-19)A total synthesis of the fungal-derived natural prod-uct pestynol is reported via a convergent chemoenzymatic ap-proach from the readily available precursors geranyl bromide,ethyl acetoacetate, trimethylsilylacetylene, and bromobenzene. Synthetic (–)-pestynol proved to be identical in all respects to thenatural material, allowing confirmation of the structure includ-ing absolute stereochemistry.
Preparation of Rearranged Allylic Isocyanates from the Reaction of Allylic Alcohols with 1-Cyano-4-dimethylaminopyridinium BromideBaidilov, Daler; Makarova, Mariia; Rycek, Lukas; Hudlicky, Tomas (Thieme, 2018-10-11)A shorter and less costly alternative to Ichikawa’s [1,3]-transposition protocol for cyanates to isocyanates is described.