Organic letters

SiMe3-based homologation-epoxidation-cyclization strategy for ladder thp synthesis

TP Heffron, TF Jamison

Index: Heffron, Timothy P.; Jamison, Timothy F. Organic Letters, 2003 , vol. 5, # 13 p. 2339 - 2342

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Citation Number: 47

Abstract

A trimethylsilyl (SiMe3) 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.

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