Related Experiment Videos
SiMe3-based homologation-epoxidation-cyclization strategy for ladder THP synthesis
Timothy P Heffron1, Timothy F Jamison
1Massachusetts Institute of Technology, Department of Chemistry, Cambridge, MA 02139, USA.
Organic Letters
|June 21, 2003
Abstract:
A trimethylsilyl (SiMe(3)) group is the basis of a strategy that emulates the three fundamental proposed processes in ladder polyether biosynthesis: chain homologation, stereoselective epoxidation (>95% ee or >95:5 dr), and endo-selective, stereospecific (inversion) hydroxyepoxide cyclization (>95:5 endo:exo, >95% dr). A tris-THP was synthesized in 18 total operations from commercial materials using this approach. [reaction: see text]