Cobalt versus Osmium: Control of Both trans and cis Selectivity in Construction of the EFG Rings of Pectenotoxin 4.
Ahria RoushanbakhtiYifan LiuPaul C M WinshipMichael J TuckerWasim M AkhtarDaryl S WalterGail WrigleyTimothy J DonohoePublished in: Angewandte Chemie (International ed. in English) (2017)
Catalytic oxidative cyclisation reactions have been employed for the synthesis of the E and F rings of the complex natural product target pectenotoxin 4. The choice of metal catalyst (cobalt- or osmium-based) allowed for the formation of THF rings with either trans or cis stereoselectivity. Fragment union using a modified Julia reaction then enabled the synthesis of an advanced synthetic intermediate containing the EF and G rings of the target.