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A new route to 3-deoxy-d-manno2-octulosonic acid: felkin-anh rule in radical chemistry

✍ Scribed by Bernd Giese; Bertrand Carboni; Thomas Göbel; Ralf Muhn; Frank Wetterich


Book ID
104215739
Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
248 KB
Volume
33
Category
Article
ISSN
0040-4039

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✦ Synopsis


Abstmck Arabinosyl mbalt complex 5 and silylated pyravate 6 give under radical condition the chain elongated sugar derivative 7. a precursor of KIWI (4). The intermediite radical 8 reacts stereoselectively with BKCl3 according to the Felkin-Anh rule.


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Treatment of 2,3:5,6-di-0-isopropylidene-D-mannitol with thionyl chloride followed by oxidation gave the corresponding 1,4-cyclic sulfate. Ring opening of the cyclic sulfate with the anion of ethyl 1,3-dithiane-2-carboxylate, and subsequent acidolysis and unmasking of the thioketal, afforded ethyl 4