Synthesis of 1, 2, 4-trioxepanes via application of thiol-olefin Co-oxygenation methodology

…, J Davies, G Labat, JF Rossignol, PM O'Neill

Index: Amewu, Richard; Stachulski, Andrew V.; Berry, Neil G.; Ward, Stephen A.; Davies, Jill; Labat, Gael; Rossignol, Jean-Francois; O'Neill, Paul M. Bioorganic and Medicinal Chemistry Letters, 2006 , vol. 16, # 23 p. 6124 - 6130

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Citation Number: 17

Abstract

Thiol-olefin co-oxygenation (TOCO) of substituted allylic alcohols generates β-hydroxy peroxides that can be condensed in situ with various ketones, to afford a series of functionalised 1, 2, 4-trioxepanes in good yields. Manipulation of the phenylsulfenyl group in 8a–8c allows for convenient modification to the spiro-trioxepane substituents. Surprisingly, and in contrast to the 1, 2, 4-trioxanes examined, 1, 2, 4-trioxepanes are inactive as ...