Synthesis of the tetracyclic core of <i>Illicium</i> sesquiterpenes using an organocatalyzed asymmetric Robinson annulation

Trzoss, Lynnie; Xu, Jing; Lacoske, Michelle H.; Theodorakis, Emmanuel A.

doi:10.3762/bjoc.9.126

Cited by 10 publications

(7 citation statements)

References 115 publications

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“…In the HMBC spectrum, the long-range correlations of H-13/C-9 and C-2, H-2/C-9 and C-4, H-3/C-4 and C-9, revealed the presence of a five-membered ring (A ring) ( Figure 2). The other HMBC correlations and the 13 C NMR chemical shift values were similar to those of jiadifenone (4), which has the same B and C rings as majucin-type sesquiterpenoids without the δ-lactone ring. The relative configuration of compound 3 was defined by a NOESY experiment ( Figure 4) in which correlations between H-1 and H-7, H-7 and H-11 were exhibited, indicating that compound 3 possessed the same relative configuration as those of jiadifenone (4).…”

Section: Resultssupporting

confidence: 53%

“…[3] This family of neurotrophic sesquiterpenes has been the focus of extensive synthetic studies. [4] Many compounds from natural sources and related molecules, such as sesquiterpenoids, [5,6] diterpenoids, [7] steroids and alkaloids exhibit potentiating activities of NGF-induced neurite outgrowth in PC12 cells. [8,9] To further research for agents that promote regeneration and growth of neurons, we further investigated the chemical constituents of the fruits of I. jiadifengpi collected in the south China, resulting in the first isolation of two seco-prezizaane-type sesquiterpenoids named jiadifenlactone acid monomethyl ester (1) and jiadifenin (3), respectively.…”

Section: Introductionmentioning

confidence: 99%

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Sesquiterpenoids of Illicium jiadifengpi and Their Effects on NGF‐induced Neurite Outgrowth in PC12 Cells

Liu

et al. 2017

Chin. J. Chem.

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Two new compounds, jiadifenlactone acid monomethyl ester (1) and jiadifenin (3), and five known compounds were isolated from the fruits of I. jiadifengpi. Their structures were determined using spectroscopic techniques, including 1D, 2D NMR and HR‐ESI‐MS experiments. The relative stereochemistry of jiadifenlactone acid monometheyl ester (1) was further confirmed by X‐ray crystallographic data. All isolates were evaluated for their effects on nerve growth factor (NGF)‐mediated neurite outgrowth in pheochromocytoma (PC12) cells and two compounds showed promoting effects.

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Section: Resultssupporting

confidence: 53%

Section: Introductionmentioning

confidence: 99%

Sesquiterpenoids of Illicium jiadifengpi and Their Effects on NGF‐induced Neurite Outgrowth in PC12 Cells

Liu

et al. 2017

Chin. J. Chem.

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“…Since 2016, our group at the Forensic Science Center (FSC) at the Lawrence Livermore National Laboratory (LLNL) has reported the use of the salt TMO in the derivatization of phosphonic acids related to OPNAs [ 85 , 86 , 87 ] ( Figure 4 ). Our interest in this salt originated from our knowledge that alkyloxonium salts, out of which Meerwein’s reagent (triethyloxonium tetrafluoroborate) is the most famous, have found a plethora of applications in the field of total synthesis due to their reactivity and thus their ability to alkylate hindered hydroxyl [ 88 , 89 , 90 ] and carboxylic acid groups [ 91 , 92 , 93 ]. Some key characteristics of the reagent sparked our interest in testing as potential option to DM during analyte methylation reactions for GC-MS analyses.…”

Section: Methylation Methodsmentioning

confidence: 99%

Analysis of Organophosphorus-Based Nerve Agent Degradation Products by Gas Chromatography-Mass Spectrometry (GC-MS): Current Derivatization Reactions in the Analytical Chemist’s Toolbox

Valdez

Leif

2021

Molecules

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The field of gas chromatography-mass spectrometry (GC-MS) in the analysis of chemical warfare agents (CWAs), specifically those involving the organophosphorus-based nerve agents (OPNAs), is a continually evolving and dynamic area of research. The ever-present interest in this field within analytical chemistry is driven by the constant threat posed by these lethal CWAs, highlighted by their use during the Tokyo subway attack in 1995, their deliberate use on civilians in Syria in 2013, and their use in the poisoning of Sergei and Yulia Skripal in Great Britain in 2018 and Alexei Navalny in 2020. These events coupled with their potential for mass destruction only serve to stress the importance of developing methods for their rapid and unambiguous detection. Although the direct detection of OPNAs is possible by GC-MS, in most instances, the analytical chemist must rely on the detection of the products arising from their degradation. To this end, derivatization reactions mainly in the form of silylations and alkylations employing a vast array of reagents have played a pivotal role in the efficient detection of these products that can be used retrospectively to identify the original OPNA.

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“…Notably, the Danishefsky [87] and Theodorakis research groups [95] have independently performed such studies on the jiadifenin structural motif and have identified several compounds, such as 75 , ODNM ( 16 ), 76 , and 77 , which are more potent than the parent natural products in promoting neurite outgrowth. The neurotrophic effects were evaluated by measuring the stimulation of NGF-mediated neurite outgrowth in PC-12 cells.…”

Section: Neurotrophic Natural Productsmentioning

confidence: 99%

Neurotrophic Natural Products: Chemistry and Biology

2013

Self Cite

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Neurodegenerative diseases and spinal cord injury affect approximately 50 million people worldwide, bringing the total healthcare cost to over 600 billion dollars per year. Nervous system growth factors, that is, neurotrophins, are a potential solution to these disorders, since they could promote nerve regeneration. An average of 500 publications per year attests to the significance of neurotrophins in biomedical sciences and underlines their potential for therapeutic applications. Nonetheless, the poor pharmacokinetic profile of neurotrophins severely restricts their clinical use. On the other hand, small molecules that modulate neurotrophic activity offer a promising therapeutic approach against neurological disorders. Nature has provided an impressive array of natural products that have potent neurotrophic activities. This Review highlights the current synthetic strategies toward these compounds and summarizes their ability to induce neuronal growth and rehabilitation. It is anticipated that neurotrophic natural products could be used not only as starting points in drug design but also as tools to study the next frontier in biomedical sciences: the brain activity map project.

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Synthesis of the tetracyclic core of Illicium sesquiterpenes using an organocatalyzed asymmetric Robinson annulation

Cited by 10 publications

References 115 publications

Sesquiterpenoids of Illicium jiadifengpi and Their Effects on NGF‐induced Neurite Outgrowth in PC12 Cells

Sesquiterpenoids of Illicium jiadifengpi and Their Effects on NGF‐induced Neurite Outgrowth in PC12 Cells

Analysis of Organophosphorus-Based Nerve Agent Degradation Products by Gas Chromatography-Mass Spectrometry (GC-MS): Current Derivatization Reactions in the Analytical Chemist’s Toolbox

Neurotrophic Natural Products: Chemistry and Biology

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