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  • Asymmetric total synthesis and absolute stereochemistry of the neuroactive marine macrolide palmyrolide A.

Asymmetric total synthesis and absolute stereochemistry of the neuroactive marine macrolide palmyrolide A.

Organic letters (2012-04-06)
Rodolfo Tello-Aburto, Emily M Johnson, Cheyenne K Valdez, William A Maio
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Copper(I) iodide ChemBeads
Sigma-Aldrich
Copper(I) iodide, 98%
Sigma-Aldrich
Copper(I) iodide, purum, ≥99.5%
Sigma-Aldrich
Copper(I) iodide, 99.999% trace metals basis