A concise stereoselective synthesis of (-)-lentiginosine, an iminosugar endowed with an interesting proapoptotic activity, has been accomplished using an enantiopure pyrroline N-oxide building block derived from D-tartaric acid. Key steps are a totally diastereoselective nucleophilic addition to the cyclic nitrone followed by a combination of two simultaneous and two tandem reactions occurring under the same conditions in a single laboratory operation. Natural (+)-lentiginosine can be synthesized by the same method but starting from L-tartaric acid.
A Stereoselective Synthesis of Lentiginosine / Cordero, Franca M; Vurchio, Carolina; Brandi, Alberto. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 81:(2016), pp. 1661-1664. [10.1021/acs.joc.5b02804]
A Stereoselective Synthesis of Lentiginosine
CORDERO, FRANCA MARIA;VURCHIO, CAROLINA;BRANDI, ALBERTO
2016
Abstract
A concise stereoselective synthesis of (-)-lentiginosine, an iminosugar endowed with an interesting proapoptotic activity, has been accomplished using an enantiopure pyrroline N-oxide building block derived from D-tartaric acid. Key steps are a totally diastereoselective nucleophilic addition to the cyclic nitrone followed by a combination of two simultaneous and two tandem reactions occurring under the same conditions in a single laboratory operation. Natural (+)-lentiginosine can be synthesized by the same method but starting from L-tartaric acid.File | Dimensione | Formato | |
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