Biomedical subjects
Publications and source records attributed to David Orain.
[reaction: see text] The synthesis of an indole diazabicyclo[3.2.2]nonedione derivative was achieved in a few steps starting from L-tryptophan. Reduction with borane-THF complex leads to fragmentation of the bicycle and the stereoselective formation of an azepinoindole derivative was observed.
The first synthesis of a rotaxane by solid phase chemistry has been achieved, using the resin bead as a 'Mega' stopper during the synthesis. One of the advantages of this methodology over traditional solution routes include the ability to use mass action to drive the chemistry, without complicating the purification process.
Functionalized deuterioallylic compounds were efficiently prepared by reaction of the corresponding propargylic derivative with the Schwartz reagent followed by hydrolysis of the adduct with D(2)O. The Z-3-deuterio-2-propenylstannane, prepared in pure form for the first time, is a useful reagent for the preparation of deuterioallylic compounds which cannot be synthesized by hydrozirconation of the corresponding derivatives.
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