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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Spirocyclic iridoid alkaloids from Plumeria rubra
Xin-Hua Gao1, Bin Zhou1,2, Flavia M Zimbres3
1State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China. jmyue@simm.ac.cn.
None:
Plumerianoids A-D (1-4) with a new intact spirocyclic iridoid alkaloid skeleton, along with a new degraded alkaloid 8-epi-plumerianine (5), and a known one (6), were isolated and characterized from Plumeria rubra. The structure of 6 was revised as (8R,13S)-plumerianine. These alkaloids consist of three epimeric pairs (1/2, 3/4, and 5/6), exhibiting virtually identical NMR spectra within each pair. Furthermore, the electronic circular dichroism (ECD) curves of each epimeric pair are roughly mirror-like, reminiscent of enantiomers. This study calls for attention on the structural elucidation of special compound classes when the associated chiral centers are far away from the chromophores and/or at the terminal of the molecules. In addition, compound 3 exhibited moderate antiplasmodial activity.
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