Short Synthesis of (+)-1-Deoxynojirimycin via a Diastereoselective Reductive Coupling of Alkyne and α-Chiral Aldehyde

Abstract

A short, highly diastereoselective synthesis of (+)-1-deoxynojirimycin from readily available l-isoserine with overall yield of 32.0% in eight steps is described. The key step includes a diastereoselective syn-coupling reaction of Cbz-protected (S)-iso­serinal acetonide 6 and vinylzinc nucleophile, generated conveniently from a protected propargyl alcohol 7 by a hydrozirconation-transmetalation sequence. Significantly, not only does this simple flexible strategy provide a concise approach to (+)-1-deoxynojirimycin, but it also can readily be adopted for the synthesis of other stereoisomers of the 1-deoxynojirimycin family from l- or d-iso­serine through different coupling conditions and stereoselective ­epoxidation of allylic alcohol 4 by the same procedures.

(+)-1-deoxynojirimycin - diastereoselective coupling - l-isoserine - diastereoselective synthesis - chelation-control transition state

References and Notes

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Figure 2

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