Literature DB >> 14656117

Hydroperoxide and endoperoxide lactones from photooxygenation of 3-alkylidenedihydrofuran-2,4-diones.

Rainer Schobert1, Ralf Stehle, Wolfgang Milius.   

Abstract

3-Alkylidenedihydrofuran-2,4-diones 1 can be photooxygenated with O(2)/TBHP to hydroperoxides 3 which slowly decompose to diols 5. Stable endoperoxides 4 are best prepared by photooxygenation of 1 with 2 equiv of O(2) in the presence of CuSO(4) and p-TosOH following a nonradical mechanism. They are rapidly reduced by anhydrous FeBr(2) to give butenolide 9 indicating a potential antimalarial activity.

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Year:  2003        PMID: 14656117     DOI: 10.1021/jo030270a

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  2 in total

Review 1.  Domino syntheses of bioactive tetronic and tetramic acids.

Authors:  Rainer Schobert
Journal:  Naturwissenschaften       Date:  2006-08-31

Review 2.  Synthesis of five- and six-membered cyclic organic peroxides: Key transformations into peroxide ring-retaining products.

Authors:  Alexander O Terent'ev; Dmitry A Borisov; Vera A Vil'; Valery M Dembitsky
Journal:  Beilstein J Org Chem       Date:  2014-01-08       Impact factor: 2.883

  2 in total

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