Sinefungin has been synthesized from D-ribose, L-ornithine, and adenine. L-Ornithine was converted to its &nitro analogue 10, which was coupled to the ribose derived aldehyde 11 by a potassium fluoride catalyzed nitro-aldol reaction., The resulting nitro alcohol 12 was further transformed by dehydration and reduction of the nitrovinyl intermediate to the oxime, which was oxidatively cleaved to ketone 16. The proper (S) stereochemistry at C-6 resulted from ...
![1,1-dimethylethyl [methyl-6-nitro-5,6,7,8,9,-pentadeoxy-9(S)-[[(4-methylphenyl)sulfonyl]amino]-2,3-O-(1-methyl-ethylidene)-β-D-ribo-dec-5-enofuranosid]uronates Structure](https://image.chemsrc.com/caspic/228/124288-77-3.png)
![1,1-dimethylethyl [methyl-6-hydroximino-5,6,7,8,9-pentadeoxy-9(S)-[[(4-methylphenyl)sulfonyl]amino]-2,3-O-(1-methylethylidene)-β-D-ribo-dec-5-enofuranosid]uronates Structure](https://image.chemsrc.com/caspic/190/124288-78-4.png)
![(2S,6R)-tert-butyl 6-hydroxy-6-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-(4-methylphenylsulfonamido)-5-nitrohexanoate Structure](https://image.chemsrc.com/caspic/266/124288-76-2.png)
