Issue 4, 2016
From the journal:

Organic & Biomolecular Chemistry

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

Jaehoon Sim,a   Inah Yoon,a   Hwayoung Yun,b   Hongchan Ana  and  Young-Ger Suh*a  

* Corresponding authors

a College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 151-742, Korea
E-mail: ygsuh@snu.ac.kr

b College of Pharmacy, Pusan National University, Geumjeong-gu, Busan 609-735, Korea

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

DOI
https://doi.org/10.1039/C5OB02147B
Article type
Paper
Submitted
18 Oct 2015
Accepted
16 Nov 2015
First published
17 Nov 2015

Org. Biomol. Chem., 2016,14, 1244-1251

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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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