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Synthesis of the New 7 S ‐Aminolentiginosine and Derivatives
Author(s) -
Cordero Franca M.,
Bonanno Paola,
Neudeck Sven,
Vurchio Carolina,
Brandi Alberto
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800806
Subject(s) - chemistry , cycloaddition , tartaric acid , 1,3 dipolar cycloaddition , copper , pyrroline , combinatorial chemistry , organic chemistry , medicinal chemistry , stereochemistry , catalysis , citric acid
The new 7 S ‐aminolentiginosine has been synthesized by a diastereoselective 1,3‐dipolar cycloaddition strategy starting from 3,4‐dihydroxylated pyrroline N ‐oxides derived from L ‐tartaric acid in thirteen steps. The intermediate 7 S ‐azidolentiginosine undergoes efficiently copper(I)‐catalysed Huisgen cycloadditions to alkynes.