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A three-component, titanium-mediated synthesis of α-branched N-acylamines from commercial or readily accessible amides, aldehydes, and organometallic reagents is reported. The transformation proceeds under mild reaction conditions and tolerates a variety of functional groups (including nitrile, carbamate, olefin, basic amine, furan, and other sensitive heteroaromatics) to generate a large umbrella of α-branched N-acylamine products in high yields. The operationally practical procedure enables the use of this method in parallel chemical synthesis, a valuable feature that can facilitate the screening of bioactive molecules by medicinal chemists. [ABSTRACT FROM AUTHOR]

A convergent, efficient synthesis of syringolin A has been accomplished in 13 steps from commercially available materials, Garner’s aldehyde and l-valine. The unnatural 3,4-dehydrolysine fragment was prepared using successive Johnson−Claisen/Curtius rearrangement reactions. The macrolactamization and late-stage introduction of the side chain will provide convenient access to analogues of this promising proteasome inhibitor. [ABSTRACT FROM AUTHOR]