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Synthesis 1987; 1987(12): 1088-1091
DOI: 10.1055/s-1987-28177
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Sulfoxide-Directed Lactonization: Asymmetric Synthesis of Porosin Intermediates

Joseph P. Marino* , Roberto Fernández de la Pradilla, Edgardo Laborde
  • *Department of Chemistry, The University of Michigan, Ann Arbor, MI 48 109, U.S.A.
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Publikationsdatum:
20. August 2002 (online)

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The application of a chiral sulfoxide-directed lactonization to the synthesis of a precursor of the neolignan porosin, in optically active form, is described. The methodology provides an efficient access to 3,4-disubstituted γ-butyrolactones with complete control of the relative and absolute stereochemistry at C-3 and C-4. The scope and generality of the method are disclosed and experimental details are presented pertaining to the preparation of all chiral intermediates.