Stereospecific double glycolisation of 1,2-dihydropyridines with OsO4. Synthesis of (±) aminoarabinose- and of (±) aminoaltrose derivatives [1].

Nitroso Diels-Alder Cycloadducts Derived From N-Acyl-1,2-dihydropyridines as a New Platform to Molecular Diversity

“…This behavior was ascribed to the lower electron-withdrawing effect of the carbonyl attached to N 3 , which is not sufficient electron-withdrawing to trigger the C 4 -N 3 shift necessary for the rearrangement reaction. The formation of a dioxazine ring by [3,3]-sigmatropic rearrangement was also reported by Streith and co-workers in 1990 [39]. However, the corresponding experimental procedure was very poorly defined, and the authors simply indicated that the treatment of a dichloromethane solution of NDA cycloadduct 5b with a large amount of silicic acid afforded stereospecifically the dioxazine 27b.…”

“…To our knowledge, the first and unique example of a reductive manipulation of a bicyclic 1,4,2-dioxazine have been described in the previous paragraph for the synthesis of iminosugars (see Scheme 14) [39]. Basically, twenty-eight years later, Pineschi and co-workers chanced upon a diversification on the behavior of dioxazines in the presence of different combinations of hydride sources and/or metal catalysts [45].…”

Biological activities of 3,4,5‐trihydroxypiperidines and their N‐ and O‐derivatives

“…Backenstrass and Streith [38] evaluated these molecules 61–63 for their antiviral activity in CEM‐T4 cells infected with HIV 1 (strain GB 8). Their activity was assessed by light microscopic measurement of inhibition of syncytium formation.…”

Synthetic Routes to 3,4,5‐Trihydroxypiperidines via Stereoselective and Biocatalysed Protocols, and Strategies to N‐ and O‐Derivatisation

“…Backenstrass and Streith reported a stereospecific double dihydroxylation of 1,2‐dihydropyridines 15a and 15b with osmium tetroxide which afforded stereospecifically products 16a and 16b . The second osmylation step occurs anti with respect to the first one, with no other tetrol isolated from this reaction.…”

“…A reductive amination approach between suitable aldehydes and the iminosugar amine group was employed for the N ‐alkylation of 3D to target molecules 68 – 70 under catalytic hydrogenation conditions, which proceeded in quantitative yields in all cases, and of meso ‐2 to final product 71 utilising the borane · pyridine reagent in MeOH‐phosphate buffer (pH 7.2), which proceeded in 80 % yield (Scheme ) …”