Double stereodifferentiating Dreiding-Schmidt reactions
1994; Elsevier BV; Volume: 50; Issue: 4 Linguagem: Inglês
10.1016/s0040-4020(01)80822-x
ISSN1464-5416
AutoresRené Csük, Brigitte I. Glänzer, Hu Zhong, Roland Boese,
Tópico(s)Sesquiterpenes and Asteraceae Studies
ResumoSpiroanellated carbohydrate-derived α-methylene-γ-butyrolactones with an additional stereogenic centre in the β-position of the anellated lactone ring and spiroanellated α-alkylidene-γ-butyrolactones were obtained in a stereoselective manner by Dreiding-Schmidt reactions of the deoxy-uloside 1 or of 2,3-O-isopropylidene-D-erythronolactone (2) with the corresponding (Z) alkyl-2-bromomethyl-2-alkenoates in the presence of the highly reactive zinc-silver/graphite surface compound.
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