Abstract
In this contribution, we report novel palladium-catalyzed carbonylative cascade approaches to highly functionalized polyheterocyclic structures. The Pd-catalyzed carbonylative process involves the regioselective insertion of one to three CO molecules and the sequential ordered formation of up to eight new bonds (one C–O, two C–C, five C–N). The exclusive formation of six-membered heterocycles is elucidated by detailed modeling studies.
Highlights
In this contribution, we report novel palladiumcatalyzed carbonylative cascade approaches to highly functionalized polyheterocyclic structures
An impressive example that mimics the natural biosynthesis of tetracyclic lanosterol from squalene is the Pd-catalyzed carbonylative pentacyclization reaction reported by Negishi and co-workers as early as 1994 (Figure 1).[3]
We have recently reported efficient palladium-catalyzed syntheses of indole-fused furanones[6] and furofuranone derivatives[7] as examples of successful carbonylative cascade double-cyclization processes from easy accessible multifunctional precursors to complex molecular structures.[8]
Summary
Francesco Pancrazzi − Department of Chemistry, Life Sciences and Environmental Sustainability (SCVSA), University of Parma, 43124 Parma, Italy. Nicolò Sarti − Department of Chemistry, Life Sciences and Environmental Sustainability (SCVSA), University of Parma, 43124 Parma, Italy. Mazzeo − Department of Chemistry, Life Sciences and Environmental Sustainability (SCVSA), University of Parma, 43124 Parma, Italy. Alessia Bacchi − Department of Chemistry, Life Sciences and Environmental Sustainability (SCVSA), University of Parma, 43124 Parma, Italy; CIRCC, 70126 Bari, Italy; orcid.org/ 0000-0001-5675-9372. Raffaella Mancuso − Department of Chemistry and Chemical Technologies, University of Calabria, 87036 Arcavacata di Rende, Cosenza, Italy; orcid.org/0000-0001-7514-6096. Bartolo Gabriele − Department of Chemistry and Chemical Technologies, University of Calabria, 87036 Arcavacata di Rende, Cosenza, Italy; orcid.org/0000-0003-4582-1489. Mirco Costa − Department of Chemistry, Life Sciences and Environmental Sustainability (SCVSA), University of Parma, 43124 Parma, Italy.
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