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Issue 4, 2016
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Divergent synthetic route to new cyclopenta[c]pyran iridoids: syntheses of jatamanin A, F, G and J, gastrolactone and nepetalactone

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Abstract

Six natural iridoids including jatamanin A, F, G and J, gastrolactone and nepetalactone have been synthesized via the efficient transformation of a core cyclopenta[c]pyran intermediate. Key features of the syntheses include the stereoselective construction of the core cyclopenta[c]pyran skeleton of the iridoid lactones via a Pd(0)-catalyzed intramolecular allylic alkylation, and the facile transformation of the common intermediate into natural iridoids.

Graphical abstract: Divergent synthetic route to new cyclopenta[c]pyran iridoids: syntheses of jatamanin A, F, G and J, gastrolactone and nepetalactone

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Article information


Submitted
18 Oct 2015
Accepted
16 Nov 2015
First published
17 Nov 2015

Org. Biomol. Chem., 2016,14, 1244-1251
Article type
Paper

Divergent synthetic route to new cyclopenta[c]pyran iridoids: syntheses of jatamanin A, F, G and J, gastrolactone and nepetalactone

J. Sim, I. Yoon, H. Yun, H. An and Y. Suh, Org. Biomol. Chem., 2016, 14, 1244
DOI: 10.1039/C5OB02147B

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