Issue 27, 2019

First total synthesis of ent-asperparaline C and assignment of the absolute configuration of asperparaline C

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.

Graphical abstract: First total synthesis of ent-asperparaline C and assignment of the absolute configuration of asperparaline C

Supplementary files

Article information

Article type
Communication
Submitted
01 fev 2019
Accepted
08 mar 2019
First published
08 mar 2019

Chem. Commun., 2019,55, 3931-3934

First total synthesis of ent-asperparaline C and assignment of the absolute configuration of asperparaline C

I. Dokli, R. Pohl, B. Klepetářová and U. Jahn, Chem. Commun., 2019, 55, 3931 DOI: 10.1039/C9CC00945K

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