Synthetic (±)-Axinellamines Deficient in Halogen

Hiding in plain sight: Tailored synthetic dimers of the natural product dispacamide exist as a dynamic set of structural isomers. These materials isomerize readily to unveil a spirocyclic glycocyamidine from which ring systems common to complex pyrrole/imidazole alkaloids can be derived. Fully synth...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2012-04, Vol.51 (18), p.4340-4343
Main Authors: Ding, Hui, Roberts, Andrew G., Harran, Patrick G.
Format: Article
Language:English
Subjects:
Alkaloids
axinellamines
Congeners
Dimers
dispacamide
Dynamical systems
Dynamics
Halogens
Halogens - chemistry
Imidazole
Imidazoles - chemical synthesis
Imidazoles - chemistry
Isomers
Molecular Structure
natural products
Pyrroles
Pyrroles - chemical synthesis
Pyrroles - chemistry
spiro compounds
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Summary:Hiding in plain sight: Tailored synthetic dimers of the natural product dispacamide exist as a dynamic set of structural isomers. These materials isomerize readily to unveil a spirocyclic glycocyamidine from which ring systems common to complex pyrrole/imidazole alkaloids can be derived. Fully synthetic axinellamine congeners have been prepared in this way (see scheme), wherein a host of unusual and unanticipated reactions are employed.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201200205