Stereoselective Synthesis of a Bengamide E Derivative Through S_E′Addition of a Chiral γ-Alkoxy Allylic Stannane to a Tartrate-Derived α, β-Dialkoxy Aldehyde

1 January 1992

journal article
letter
Published by Georg Thieme Verlag KG in Synlett

Vol. 1992 (12) , 1007-1008
https://doi.org/10.1055/s-1992-21565

Abstract

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.

Keywords

ALKOXY
TREATMENT
BENGAMIDE
ALLYLIC
ALDEHYDE
STANNANE
CONVERTED
CHIRAL

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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

Abstract

Keywords

Stereoselective Synthesis of a Bengamide E Derivative Through S_E′Addition of a Chiral γ-Alkoxy Allylic Stannane to a Tartrate-Derived α, β-Dialkoxy Aldehyde