Asymmetric Total Synthesis and Absolute Stereochemistry of the Neuroactive Marine Macrolide Palmyrolide A

The first asymmetric total synthesis and determination of the absolute configuration for the neuroactive marine macrolide palmyrolide A is described. The highlight of the synthesis is macrocyclization via trans-enamide formation catalyzed by copper(I) iodide and cesium carbonate. Comparison with the...

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Bibliographic Details
Published in:Organic letters 2012-04, Vol.14 (8), p.2150-2153
Main Authors: Tello-Aburto, Rodolfo, Johnson, Emily M, Valdez, Cheyenne K, Maio, William A
Format: Article
Language:English
Subjects:
Catalysis
Copper - chemistry
Iodides - chemistry
Macrolides - chemical synthesis
Macrolides - chemistry
Marine Biology
Molecular Structure
Nervous System - drug effects
Stereoisomerism
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Summary:The first asymmetric total synthesis and determination of the absolute configuration for the neuroactive marine macrolide palmyrolide A is described. The highlight of the synthesis is macrocyclization via trans-enamide formation catalyzed by copper(I) iodide and cesium carbonate. Comparison with the authentic spectral data confirms the synthesis of (+)-ent-palmyrolide A.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol300673m