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Synthesis 1991; 1991(9): 731-734
DOI: 10.1055/s-1991-26558
DOI: 10.1055/s-1991-26558
paper
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Neue C3-Bausteine zur Synthese von Naturstoffen: (R)-Glycidaldehyddiethyldithioacetal und (R)-Glycidaldehyddimethylacetal
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Publication History
Publication Date:
29 April 2002 (online)
New C3-synthons for the Synthesis of Natural Products: (R)-Glycidaldehyde Diethyl Dithioacetal and (R)-Glycidaldehyde Dimethyl Acetal The glycidaldehyde acetals (R)-1,1-bis(ethylthio)-2,3-epoxypropane (5) and (R)-2,3-epoxy-1,1-dimethoxypropane (9) were obtained from (R)-2,3-O-isopropylideneglyceraldehyde [(4R)-2,2-dimethyl-1,3-dioxolane-4-carboxaldehyde] based on D-mannitol. The applicability of glycidaldehyde acetal 5 as a useful template for the preparation of natural products has been shown by the synthesis of (2R,4Z)-2-(tert-butyldiphenylsiloxy)-4-decenal (13), the key intermediate for LTB4 and 12(R)-HETE.