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Synlett 1992; 1992(12): 1007-1008
DOI: 10.1055/s-1992-21565
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Stereoselective Synthesis of a Bengamide E Derivative Through SE′ Addition of a Chiral γ-Alkoxy Allylic Stannane to a Tartrate-Derived α, β-Dialkoxy Aldehyde

James A. Marshall* , George P. Luke
  • *Department of Chemistry and Biochemistry, The University of South Carolina, Columbia, South Carolina 29208, USA
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Publication Date:
08 March 2002 (online)

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Addition of the racemic γ-alkoxy allylic stannane 13, in three-fold excess, to the tartrate-derived aldehyde 9 in the presence of MgBr2 afforded ester 14 and lactones 15 and 16 as a separable 1.2:1.4:1 mixture in 90% yield. The mixture of 14 and 15 was converted to the bengamide E precursor 21upon treatment with (S)-α-aminocaprolactam and Me3Al.