Tandem Stille/Suzuki-Miyaura coupling of a hetero-bis-metalated diene. Rapid, one-pot assembly of polyene systems.
[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.
Coleman
Robert S
RS
Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA. coleman@chemistry.ohio-state.edu
Walczak
Matthew C
MC
D002070:Butadienes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D005670:Fusarium / Q000737:chemistry*; D007202:Indicators and Reagents; D011090:Polyenes / Q000138:chemical synthesis* / Q000737:chemistry
D002070:Butadienes; D007202:Indicators and Reagents; D011090:Polyenes