Stereocontrolled Assembly of Tetrasubstituted Tetrahydrofurans: A Concise Synthesis of Virgatusin
2005; American Chemical Society; Volume: 7; Issue: 17 Linguagem: Inglês
10.1021/ol051292h
ISSN1523-7060
AutoresTito Akindele, Stephen P. Marsden, John G. Cumming,
Tópico(s)Plant-derived Lignans Synthesis and Bioactivity
ResumoThe condensation of substituted allylsiloxanes with aldehydes leads to the highly stereoselective construction of 2,3,4,5-tetrasubstituted tetrahydrofurans. With electron-rich aryl and α,β-unsaturated aldehydes as substrates, the stereochemical outcome at C5 can be dictated by appropriate choice of Lewis acid. The reaction has been applied to a concise (nine step) synthesis of (+)-virgatusin (ent-1).
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