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Cover Picture: The Enantioselective Total Synthesis of Bisquinolizidine Alkaloids: A Modular “Inside‐Out” Approach (Angew. Chem. Int. Ed. 9/2018)
Author(s) -
Scharnagel Dagmar,
Goller Jessica,
Deibl Nicklas,
Milius Wolfgang,
Breuning Matthias
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201800930
Subject(s) - desymmetrization , enantioselective synthesis , annulation , enantiomer , stereochemistry , cyclopropanation , total synthesis , modular design , block (permutation group theory) , chemistry , combinatorial chemistry , mathematics , computer science , combinatorics , organic chemistry , operating system , catalysis
A modular “inside‐out” approach to 21 natural bisquinolizidine alkaloids, among them more than ten first enantioselective total syntheses, is reported by M. Breuning et al. in their Communication on page 2432 ff. Key was the successful preparation of both enantiomers of C 2 ‐symmetric 2,6‐dioxobispidine by desymmetrization and the successive α, N ‐annulation of a 2‐pyridone and endo ‐ or exo ‐fused piperidines to the chiral core building block.