Synthesis of spiroannulated and 3-arylated 1,2,4-trioxanes from mesitylol and methyl 4-hydroxytiglate by photooxygenation and peroxyacetalization.

Beilstein Journal of Organic Chemistry
Axel G GriesbeckJörg M Neudörfl

Abstract

Cycloalkanones were utilized in the Lewis acid catalyzed peroxyacetalization of ss-hydroperoxy homoallylic alcohols (prepared by the ene reaction of the allylic alcohols mesitylol and methyl 4-hydroxytiglate, respectively, with singlet oxygen) to give spiroannulated 1,2,4-trioxanes 5a-5e and 9a-9e, respectively. A second series of 3-arylated trioxanes 10a-10h, that are available from the hydroperoxy alcohol 4 and benzaldehyde derivatives, was investigated by X-ray crystallography.

References

Mar 20, 2002·Accounts of Chemical Research·Anne RobertBernard Meunier
May 28, 2004·Journal of Medicinal Chemistry·Paul M O'Neill, Gary H Posner
Jun 2, 2004·Medicinal Research Reviews·Yuanqing TangJonathan L Vennerstrom
Aug 20, 2004·Nature·Jonathan L VennerstromWilliam N Charman
Jan 25, 2005·Bioorganic & Medicinal Chemistry Letters·Axel G GriesbeckReto Brun
Feb 3, 2007·Journal of Medicinal Chemistry·Chandan SinghSunil K Puri
Aug 2, 2007·Accounts of Chemical Research·Bernard Meunier
Aug 14, 2008·Clinical Infectious Diseases : an Official Publication of the Infectious Diseases Society of America·Thomas EfferthManfred Marschall
Sep 17, 2008·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Axel G GriesbeckTamer T El-Idreesy

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Citations

Jan 24, 2014·Beilstein Journal of Organic Chemistry·Alexander O Terent'evValery M Dembitsky

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Methods Mentioned

BETA
X-ray
column chromatography

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