α-Chloronitroso compounds derived from carbohydrate ketones: cycloadditions with cyclic dienes, a synthesis of (–)-physoperuvine and a formal synthesis of (+)- …

A Hall, PD Bailey, DC Rees, GM Rosair…

Index: Hall, Adrian; Bailey, Patrick D.; Rees, David C.; Rosair, Georgina M.; Wightman, Richard H. Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 3 p. 329 - 343

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Abstract

1, 2-O-Isopropylidene-α-D-xylofuranose 9 was converted into 5-O-(tert-butyldiphenylsilyl)-3- chloro-3-deoxy-1, 2-O-isopropylidene-3-C-nitroso-α-D-xylofuranose 17 in four steps, and a similar α-chloronitroso compound 8 was synthesised from 1, 2∶ 5, 6-di-O-isopropylidene-α- D-glucofuranose 6, the structures of 8 and 17 being confirmed by X-ray crystallography. Reaction of 8 or 17 with cyclohexa-1, 3-diene in the presence of small amounts of water ...