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- W2054097321 abstract "Studies of the displacement chemistry of 1,1-difluorocyclopropyldibenzosuberanyl alcohol 4 and its activated bromide derivative 6 have led to an improved approach to anti-2, a key precursor to LY335979 3HCl (1). Bromination of either syn-4 or anti-4 gave anti-oriented 6, indicating thermodynamically controlled product stereochemistry via a stabilized 1,1-difluorohomotropylium ion intermediate. Reaction of 6 with piperazine proceeded irreversibly to provide an isomeric mixture of piperazine products, with the syn:anti product ratio increased by solvent effects. Reaction of 6 with pyridine and pyrazine, on the other hand, gave anti-pyridinium and pyrazinium salts, respectively, apparently via equilibration of initially formed syn products. Reduction of pyrazinium salt 11 with lithium borohydride/TFA provided anti-2 unaccompanied by its syn isomer. A practical and expeditious approach to 1 was derived from these new results." @default.
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- W2054097321 date "2004-10-01" @default.
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- W2054097321 title "Stereochemistry of C-6 Nucleophilic Displacements on 1,1-Difluorocyclopropyldibenzosuberanyl Substrates. An Improved Synthesis of Multidrug Resistance Modulator LY335979 Trihydrochloride" @default.
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- W2054097321 doi "https://doi.org/10.1021/jo049051v" @default.
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