ABSTRACT
Convergent and efficient syntheses of the microbial natural products gymnoconjugatin A and B are reported and were based on a linchpin coupling strategy using a boron/tin hetero-bis-metallated butadiene system.
Subject(s)
Furans/chemical synthesis , Pyrones/chemical synthesis , Boron Compounds/chemistry , Furans/chemistry , Molecular Structure , Organotin Compounds/chemistry , Pyrones/chemistry , StereoisomerismABSTRACT
Hetero-bis-metalated 1,3-butadiene is employed in the lynchpin coupling of synthetic fragments of the side chain of the antitumor agent, lucilactaene. Sequential Stille and Suzuki-Miyaura couplings interpolate this unique boron/tin diene into the pentaene chain. The total synthesis of lucilactaene was accomplished efficiently, in just eight linear steps.
Subject(s)
Cell Cycle/drug effects , Cells/metabolism , Furans/chemical synthesis , Furans/pharmacology , Pyrroles/chemical synthesis , Pyrroles/pharmacology , Tumor Suppressor Protein p53/deficiency , Cells/chemistry , Furans/chemistry , Molecular Structure , Pyrroles/chemistryABSTRACT
[structure: see text]. The synthesis of a hetero-bis-metallo 1,3-butadiene is reported, and its use as an orthogonal Stille and Suzuki-Miyaura coupling partner is detailed. The tin/boron diene participated successfully in a one-pot, sequential Stille and Suzuki-Miyaura coupling protocol, and its utility was demonstrated in the two-step construction of the pentaene side chain of the Fusarium metabolite lucilactaene.
