Journal of the American Chemical Society, Vol.119, No.32, 7499-7504, 1997
Substituted oxocanes by intramolecular allylboration reactions. Entry to an efficient synthesis of (+)-laurencin
Delta(5)-Oxocenes, such as cis-3-hydroxy-2-vinyl-Delta(5)-oxocenes, can be generated by an intramolecular aldehyde-allylboration reaction. This allowed a rapid and stereoselective access to the trisubstituted oxocene 24 which had been transformed by the Holmes group into (+)-laurencin. The key feature of this effective intramolecular allylboration reaction is that both the aldehyde and the allylboronate functionality have been generated in a masked form in situ. They are liberated by an aqueous workup which initiates the ring closure reaction.