Naturally occurring sesquiterpenes having humulane frameworks are structurally intriguing and possess significant biological profiles. Asymmetric synthesis of the alashanoids B, C, E, and F and 2,9-humuladien-6-ol-8-one is achieved for the first time through a linear synthetic strategy. Intramolecular late-stage Nozaki-Hiyama-Kishi (NHK) coupling is employed to access the eleven-membered macrocyclic core present in the target molecules. The NHK precursors are accessed using the Evans and non-Evans and -aldol reaction as a key transformation. X-ray and ECD analysis reconfirmed the synthesized compounds' structures and chirotopical properties.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/d4ob00393d | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Minor Humulane and Eremophilane Sesquiterpenoids from Syringa pinnatifolia and Their Protective Effect Against Oxidative Injuries in H9c2 Cells.
Chem Biodivers
November 2024
Research Center for Traditional Chinese Medicine Resources and Ethnic Minority Medicine, Jiangxi University of Chinese Medicine, Nanchang, 330004, PR China.
As a part of systematic research, an ongoing phytochemical investigation of the sesquiterpenoid-containing fraction led to the isolation of five new sesquiterpenoids from the peeled stems of Syringa pinnatifolia, including two pairs of enantiomeric humulane-type (±)-alashanoids A and B (1 and 2) and one eremophilane-type alashanoid C (3). These structures were elucidated by the analysis of extensive spectroscopic data, including ESI-MS and 1D and 2D NMR, and the absolute configuration was determined by comparing its experimental and calculated electronic circular dichroism and calculated NMR. These isolates exhibited moderate in vitro cardioprotective effects against oxidative injuries in H9c2 cells.
View Article and Find Full Text PDFAsymmetric total synthesis of humulane sesquiterpenoids alashanoids B, C, E, and F and 2,9-humuladien-6-ol-8-one.
Org Biomol Chem
June 2024
Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur, 721302, India.
Naturally occurring sesquiterpenes having humulane frameworks are structurally intriguing and possess significant biological profiles. Asymmetric synthesis of the alashanoids B, C, E, and F and 2,9-humuladien-6-ol-8-one is achieved for the first time through a linear synthetic strategy. Intramolecular late-stage Nozaki-Hiyama-Kishi (NHK) coupling is employed to access the eleven-membered macrocyclic core present in the target molecules.
View Article and Find Full Text PDF[Eleven new sesquiterpenoids from peeled stems of Syringa pinnatifolia].
Zhongguo Zhong Yao Za Zhi
February 2023
Modern Research Center for Traditional Chinese Medicine,Beijing Academy of Traditional Chinese Medicine, Beijing University of Chinese Medicine Beijing 100029,China.
The peeled stems of Syringa pinnatifolia(SP) is a representative Mongolian folk medicine with the effects of anti-depression, heat clearance, pain relief, and respiration improvement. It has been clinically used for the treatment of coronary heart disease, insomnia, asthma, and other cardiopulmonary diseases. As part of the systematic study on pharmacological substances of SP, 11 new sesquiterpenoids were isolated from the terpene-containing fractions of the ethanol extract of SP by liquid chromatography-mass spectrometry(LC-MS) and proton nuclear magnetic resonance(~1H-NMR) guided isolation methods.
View Article and Find Full Text PDFAlashanoids O-S, seco-Humulane and Eremophilane Sesquiterpenoids from Syringa pinnatifolia.
Chem Biodivers
February 2022
Modern Research Center for Traditional Chinese Medicine, School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing, 100029, P. R. China.
Five new sesquiterpenoids, alashanoids O-S (1-5), along with three known analogs (6-8) were isolated from the peeled stems of Syringa pinnatifolia. Their structures were elucidated by analysis of extensive spectroscopic data including ESI-MS, 1D, 2D NMR. The absolute configurations were determined by comparing its experimental and calculated electronic circular dichroism, calculated OR, calculated NMR, and single crystal X-ray diffraction data analysis.
View Article and Find Full Text PDFAlashanoids K-M, bioactive eremophilane sesquiterpenoids from .
J Asian Nat Prod Res
December 2019
School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing 100029, China.
Three new eremophilane-type sesquiterpenoids, alashanoids K-M (-), and one known analogue () were isolated from the peeled stems of . All the compounds were isolated from the genus for the first time. Structures of these compounds were established using 1D and 2D NMR and MS data.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!