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  • Title: SiMe3-based homologation-epoxidation-cyclization strategy for ladder THP synthesis.
    Author: Heffron TP, Jamison TF.
    Journal: Org Lett; 2003 Jun 26; 5(13):2339-42. PubMed ID: 12816443.
    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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