Rhynchines A-E (-), five new indole alkaloids with an unprecedented skeleton, were isolated from . The new skeleton was characterized by an indole moiety and a 2-oxa-8-azatricyclo[6,5,0,0]tridecane core, forming a unique 6/5/7/5/5 ring system. Their structures were determined by nuclear magnetic resonance, high-resolution electrospray ionization mass spectrometry, infrared spectroscopy, and calculated electronic circular dichroism (ECD) and were confirmed by X-ray crystallography. Interestingly, and showed strong inhibitory activities against the Ca3.1 calcium channel with IC values of 6.86 and 10.41 μM.
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Bioinspired Collective Total Synthesis of (±)-Rhynchines A-E.
Org Lett
April 2024
Key Laboratory of Applied Surface and Colloid Chemistry of MOE & School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 West Chang'an Ave, Xi'an 710119, China.
Herein, we present the first racemic total synthesis of the structurally complex monoterpene indole alkaloids rhynchines A-E, starting from commercially available methyl nicotinate and 3-(2-bromoethyl)-1-indole. The success of our synthesis is attributed to the utilization of a bioinspired synthetic strategy, which facilitated the rapid construction of the pentacyclic core skeleton of the target molecules through biomimetic skeletal rearrangement and late-stage C-H oxidative cyclization. Additionally, silica-gel-promoted tautomerization played a crucial role as a strategic element in the chemical synthesis of rhynchines A and B.
View Article and Find Full Text PDFRhynchines A-E: Ca3.1 Calcium Channel Blockers from .
Org Lett
December 2021
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China.
Rhynchines A-E (-), five new indole alkaloids with an unprecedented skeleton, were isolated from . The new skeleton was characterized by an indole moiety and a 2-oxa-8-azatricyclo[6,5,0,0]tridecane core, forming a unique 6/5/7/5/5 ring system. Their structures were determined by nuclear magnetic resonance, high-resolution electrospray ionization mass spectrometry, infrared spectroscopy, and calculated electronic circular dichroism (ECD) and were confirmed by X-ray crystallography.
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