18113-18-3Relevant academic research and scientific papers
Total Synthesis of Naphterpin and Marinone Natural Products
Murray, Lauren A. M.,Fallon, Thomas,Sumby, Christopher J.,George, Jonathan H.
, p. 8312 - 8315 (2019)
A concise and divergent strategy for the synthesis of the naphterpin and marinone meroterpenoid families has been developed. The approach features a succession of pericyclic reactions-an aromatic Claisen rearrangement, a retro-6?€-electrocyclization, and
Diene-Transmissive Diels-Alder Sequences with Benzynes
George, Josemon,Ward, Jas S.,Sherburn, Michael S.
, p. 7529 - 7533 (2019)
Diene-transmissive Diels-Alder (DTDA) sequences are extraordinarily powerful processes for the generation of fused bicyclic systems. Nonetheless, only stable dienophiles have previously been deployed. Herein we report DTDA sequences with a variety of substituted [3]dendralenes in the first study to deploy arynes as dienophiles. We demonstrate the one-flask generation of complex, aromatic-ring-containing, multicyclic systems of relevance to medicinal chemistry. These synthetic operations provide numerous successful examples of the otherwise challenging and rarely reported intermolecular Diels-Alder reaction of acyclic 1,3-butadienes with arynes, which is made possible due to the exalted reactivity of dendralenic dienes.
Synthesis of Two Key Fragments of the Complex Polyhalogenated Marine Meroterpenoid Azamerone
Schnell, Simon D.,Linden, Anthony,Gademann, Karl
supporting information, p. 1144 - 1147 (2019/05/16)
A concise route toward two advanced fragments in the context of the total synthesis of the unique natural product azamerone is reported. Key synthetic features include the enantioselective synthesis of an epoxysilane and its Lewis-acid-induced cyclization and the installation of the pyridazine ring via a formylation/condensation sequence. This route provides strategic insights into the chemistry of phthalazinediols, facilitating synthetic approaches toward this class of natural products.
Structure Elucidation of the Main Tetrahydroxyxanthones of Hypericum Seeds and Investigations into the Testa Structure
Lorenz, Peter,Heller, Annerose,Bunse, Marek,Heinrich, Miriam,Berger, Melanie,Conrad, Jürgen,Stintzing, Florian C.,Kammerer, Dietmar R.
, (2018/05/14)
Seeds from Hypericum species have recently been identified as an interesting source of xanthone derivatives. Extraction of seeds from H. perforatum with MeOH and subsequent concentration via polyamide adsorption yielded a fraction enriched in tetrahydroxy
A catalytic oxidation fragrant boron class compound preparing phenol method (by machine translation)
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Paragraph 0024; 0045; 0046, (2017/08/08)
The invention discloses a method for catalytic oxidation of phenolic compounds fragrant boron class compound synthesis method, the flux in the solvent in the aqueous solution, under the action of alkali, adding hydrazine hydrate or acid hydrazides catalyst, catalytic oxidation fragrant boron class compound directly for the preparation of phenolic compound. The invention of the method of preparation of the phenol compound, the catalyst is a cheap hydrazine hydrate or hydrazine compound, the oxidizing agent is atmospheric pressure of air or oxygen, the reaction does not need good and activeness metal catalyst, is extensive and stable substrate, substrate-sensitive functional group compatibility good and wide range of application. In the optimized under the reaction conditions, the yield of the target product separation up to 99%. (by machine translation)
Model Studies towards Functionalized Bisbenzannulated [5,6]-Spiroketals
Wilsdorf, Michael,Lentz, Dieter,Reissig, Hans-Ulrich
, p. 1555 - 1561 (2016/04/05)
Following up on our previous model studies on the synthesis of simple bisbenzannulated [5,6]-spiroketals we here report the preparation of new examples of this entity with a variation in their substitution pattern. The regioselective introduction of functional groups in the C-3 or C-3′ positions (rubromycin numbering) may either take place prior to the spiroketalization by α-functionalizations of the ketone moiety of the precursor or in a subsequent step by the nucleophilic substitution of the benzylic hydroxy group of the previously described C-3-hydroxylated spiroketal. By applying these methods we could synthesize new methyl-substituted, hydroxylated, halogenated and amino-substituted bisbenzannulated [5,6]-spiroketals in good overall yields. C-1 or C-3? By applying suitable methods new functionalized [5,6]-spiroketals were regioselectively generated as model compounds for rubromycin-type natural products.
Synthesis and Evaluation of Novel 7- and 8-Aminophenoxazinones for the Detection of β-Alanine Aminopeptidase Activity and the Reliable Identification of Pseudomonas aeruginosa in Clinical Samples
Bedernjak, Alexandre F.,Zaytsev, Andrey V.,Babolat, Michèle,Cellier, Marie,James, Arthur L.,Orenga, Sylvain,Perry, John D.,Groundwater, Paul W.,Anderson, Rosaleen J.
, p. 4476 - 4487 (2016/06/13)
A series of novel 8-aminophenoxazin-3-one and 7-aminophenoxazin-3-one chromogens and their corresponding β-alanine derivatives were synthesized and evaluated for their ability to detect β-alanyl aminopeptidase activity in bacteria known to hydrolyze β-ala
Unexpected hydrazine hydrate-mediated aerobic oxidation of aryl/ heteroaryl boronic acids to phenols in ambient air
Zhong, Yanzhen,Yuan, Linxin,Huang, Zheng,Gu, Wenchao,Shao, Ye,Han, Wei
, p. 33164 - 33167 (2014/08/18)
The expedient and efficient sub-stoichimetric hydrazine hydrate-mediated aerobic hydroxylation of boronic acids that proceeds in poly(ethylene glycol) (PEG-400) has been successfully developed, providing diverse phenols in high yields. And heteroaryl boronic acids are also amenable to this protocol. the Partner Organisations 2014.
Synthetic models related to methoxalen - CYP2A6 interactions. Dimethoxybenzofuran derivatives as potent and selective inhibitors of cyp2a6
Yamaguchi, Yuki,Akimoto, Ichie,Motegi, Kyoko,Yoshimura, Teruki,Wada, Keiji,Nishizono, Naozumi,Oda, Kazuaki
, p. 1727 - 1739 (2013/09/12)
The human CYP2A6 enzyme metabolizes several xenobiotics including nicotine, the addictive component in tobacco. Reduced activity of CYP2A6, either for genetic reasons or by administering inhibitors of CYP2A6, reduces tobacco smoking. The reported compound
Attempts directed towards the synthesis of intermediate (aryne)chromium complexes from aryl triflates and from (haloarene)chromium complexes
Werner, Georg,Butenschoen, Holger
, p. 3132 - 3141 (2012/06/30)
The generation of (I·6-aryne)chromium complexes as reactive intermediates was investigated in two ways. Although earlier attempts directed towards triflate eliminations from a variety of tricarbonyl(phenyl triflate)chromium complexes had failed, more electron-rich phenyl triflate complexes were considered. This was accomplished either by substitution with two methoxy groups in the arene ligand or by replacement of one of the three carbonyl ligands of the tricarbonylchromium complex with triphenylphosphane. However, the attempted elimination still did not take place; in spite of the increased electron densities in the aromatic ligands, anionic thia-Fries rearrangements were observed in high yields at -78 °C. As an alternative, elimination of lithium fluoride was tested. Tricarbonyl(2-lithiofluorobenzene) chromium(0) was generated by tin/lithium exchange. After hydrolytic workup, tricarbonyl(fluorobenzene)chromium was obtained as the main product, indicating that the lithiation step had been successful. A dimeric side product provided evidence for the intermediacy of (benzyne)tricarbonylchromium. Copyright
