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Highly functionalised cyclopentanes by radical cyclisation of unsaturated bromolactones. I preparation of 5-Deoxycarbahexofuranoses

✍ Scribed by Anne Marie Horneman; Inge Lundt

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 720 KB
Volume: 53
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(97)00319-0

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✦ Synopsis

Three carbasugars: 5-Deoxycarba-a-t.-xylo-hexofuranose, 5-deoxycarba<t-L-lyxohexofuranose and 5-deoxycarba-f3-D-lyxo-hexofuranose have been prepared starting from readily available 2,7-dibromo-2,7-dideoxy-D-glycero-D-ido-heptono-l,4-1actone and 2,7-dibromo-2,7dideoxy-D-glycero-L-gluco-heptono-l,4-1actone. 2,3-Unsaturated 7-bromo-7-deoxy-heptono-l,4lactones were prepared by reductive elimination of the starting compounds. The key step was a highly regio-and stereoselective 5-exo-trig radical cyclisation of the unsaturated bromolactones to give bicyclic cyclopentane derivatives. The lactone moiety of these compounds were reduced using H3B • S(CH3L, to give the above-mentioned carbahexofuranoses.

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