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The Enantioselective Total Synthesis of Bisquinolizidine Alkaloids : A Modular "Inside-Out" Approach

Title data

Scharnagel, Dagmar ; Goller, Jessica ; Deibl, Nicklas ; Milius, Wolfgang ; Breuning, Matthias:
The Enantioselective Total Synthesis of Bisquinolizidine Alkaloids : A Modular "Inside-Out" Approach.
In: Angewandte Chemie International Edition. Vol. 57 (2018) Issue 9 . - pp. 2432-2435.
ISSN 1521-3773
DOI: https://doi.org/10.1002/anie.201712852

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Abstract in another language

Bisquinolizidine alkaloids are characterized by a chiral bispidine core (3,7-diazabicyclo[3.3.1]nonane) to which combinations of an α,N-fused 2-pyridone, an endo- or exo-α,N-annulated piperidin(on)e, and an exo-allyl substituent are attached. We developed a modular “inside-out” approach that permits access to most members of this class. Its applicability was proven in the asymmetric synthesis of 21 natural bisquinolizidine alkaloids, among them more than ten first enantioselective total syntheses. Key steps are the first successful preparation of both enantiomers of C2-symmetric 2,6-dioxobispidine by desymmetrization of a 2,4,6,8-tetraoxo precursor, the construction of the α,N-fused 2-pyridone by using an enamine-bromoacrylic acid strategy, and the installation of endo- or, optionally, exo-annulated piperidin(on)es.

Further data

Item Type: Article in a journal
Refereed: Yes
Additional notes: Highlighted in: Synfacts 2018; 14(04): 0342. DOI: 10.1055/s-0037-1609332
Featured in: Organic Chemistry Highlights, 19.11.2018. https://www.organic-chemistry.org/Highlights/2018/19November.shtm
Featured in: Wikipedia Article "Lupanin"
https://de.wikipedia.org/wiki/Lupanin#cite_note-Angewandte_Chemie-8
Institutions of the University: Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professor Organic Chemistry > Professor Organic Chemistry - Univ.-Prof. Dr. Matthias Breuning
Result of work at the UBT: Yes
DDC Subjects: 500 Science > 540 Chemistry
Date Deposited: 11 Jan 2022 08:56
Last Modified: 11 Jan 2022 08:56
URI: https://eref.uni-bayreuth.de/id/eprint/68296