A Tactically Novel Alternative to Acyclic Stereoselection Based on the Concept of a Replicating Chiron - 1,5-C-Methyl Substitution

Article abstract of DOI:10.1016/S0040-4039(01)80903-5

A synthetic sequence is described wherein a chiral butyrolactone is used as a template to control the stereochemistry of a C-methylation process on the corresponding enolate.A sequential two-carbon homologation and replication of the butyrolactone template allows a second stereocontrolled C-methylation.The ultimate outcome is a seven carbon acyclic chain with a predicable 1,5-substitution pattern of C-methyl groups with or without an intervening hydroxyl group.