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. 2012 Apr 20;14(8):2150-3.
doi: 10.1021/ol300673m. Epub 2012 Apr 4.

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

Rodolfo Tello-Aburto  1 , Emily M Johnson, Cheyenne K Valdez, William A Maio
Affiliations

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

Rodolfo Tello-Aburto et al. Org Lett. .

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.

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Figures

Scheme 1
Scheme 1
Retrosynthetic Analysis
Scheme 2
Scheme 2
Synthesis of Cyclic Sulfate 5
Scheme 3
Scheme 3
Synthesis of Fragment 2
Scheme 4
Scheme 4
Assembly of Vinyl Iodides 3a and 3b
Scheme 5
Scheme 5
Synthesis of Macrocycles 1a and 1b
See this image and copyright information in PMC

References

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