Helvetica Chimica Acta · 1968 · 12 citations · 3 references
Natural SciencesBiochemistryChemistryBioorganic ChemistryOrganic ChemistryStructure-activity RelationshipsAddition ReactionsRetrosynthetic AnalysisEpoxide FormationPeroxy Intermediates
Abstract Through a D IELS ‐A LDER reaction between citraconic anhydride ( 1 ) and methyl resinates, the adducts 2a, b, c were obtained. The epoxide 6 , derived from 2a , by acidic methanolysis gave 7 with retention of configuration. The structure of the latter compound was demonstrated by 7 → 8 → 9 , the dilactone 9 being characterized by an electronic interaction and an «M coupling». Sodium borohydride reduced 2d and 2a , giving the diols 3d and 3a , respectively the cis ‐configuration of which was chemically demonstrated.
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