SiMe3-based homologation-epoxidation-cyclization strategy for ladder THP synthesis |
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Authors: | Heffron Timothy P Jamison Timothy F |
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Institution: | Massachusetts Institute of Technology, Department of Chemistry, Cambridge, MA 02139, USA. |
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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] |
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