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Starting with the hetero-Diels-Alder reaction of the 0-isopropylidene-protected cis-cyclohexa-3,5diene-l,2-diol with (-) -2,3: 5,6-di-O-isopropylidene-l -nitroso-a-D-manno-furanosyl chloride the optically pure (+)-endo-adduct was exclusively formed. After reduction of the NO bond and protection of the amino group, the second nitrogen function was introduced b y participation of the neighbouring trichloroacetimidate group in the addition of iodine to the C=C bond or in the epoxide opening of the corresponding tri-0-trichloroacetimidato-trans-epoxide derivative. Hydrolysis of the bicyclic di hydro-l,3-oxazoles, complete acetylation, deiodonation if necessary, and final simultaneous removal of all protective groups yielded (-) -1 ~-2,4-diamino-2,3,4-trideoxy-a//oinositol and (-) -1 ~-2,4-diamino-2,4-dideoxy-chiro-inositol in good overall yields.The absolute configuration of the hetero-Diels-Alder endo-adduct was determined by chemical transformation.

This contribution presents stereoselective routes to various cis-inos-I ,3-diamines starting from readily available cis-4-aminocyclohexenols (7) and (8). The second nitrogen function is introduced into the ring by use of intramolecular cyclisations of neighbouring trichloroacetimidate groups. Hydrolytic

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