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First total synthesis of ent-asperparaline C and assignment of the absolute configuration of asperparaline C
Irena Dokli1, Radek Pohl1, Blanka Klepetářová1
1Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo Náměstí 2, 16610 Prague 6, Czech Republic. ullrich.jahn@uochb.cas.cz.
Abstract:
The first asymmetric total synthesis of a member of the asperparaline family was accomplished and the unknown absolute configuration of asperparaline C has been determined to be all-(S). The key steps of the synthesis are an oxidative radical cyclization, a selective reduction of one of the tertiary amides, a singlet oxygen Diels-Alder reaction and a reductive spirocyclization.
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