An enantioselective synthesis of diverse N4-Boc-protected α,α-disubstituted piperazin-2-ones and tetrahydropyrimidin-2-ones using the palladiumcatalyzed decarboxylative allylic alkylation reaction has been achieved.
A nonthermodynamic array of four skipped methylene substituents on the hydrophobic tail
renders limaol, a C40-polyketide of marine origin, unique in structural terms. This
conspicuous segment was assembled by a two-directional approach and finally coupled to
the polyether domain by an allyl/alkenyl Stille reaction under neutral conditions. The
core region itself was prepared via a 3,3′-dibromo-BINOL-catalyzed asymmetric
propargylation, a gold-catalyzed spirocyclization, and introduction of the southern
sector via substrate-controlled allylation as the key steps.
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