- Studies on D-Threose Derivatives and on the Preparation of the Olivin Side Chain
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Oxidative cleavage of the D-arabinitol derivative 3 yields the dimer 5 of benzylidene D-threose.In pyridine solution D-threose (11), obtained by acid hydrolysis, predominatly represents a mixture of the anomeric furanoses 7 and 12.By either kinetic or thermodynamic isopropylidenation of the trimethylene dithioacetal 9 preparation of the terminal or the non-terminal dioxolane 14 or 16, respectively, is achieved selectively.Starting with 16 several steps lead to the crystalline 4-deoxy-D-threose trimethylene dithioacetal (25), by metallation of which the formation of a trianion could not be demonstrated.However, both the diastereomeric model compounds 28 and 30 of the olivin side chain were prepared via dimetallation of 14.
- Thiem, Joachim,Wessel, Hans-Peter
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p. 2216 - 2227
(2007/10/02)
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