402573-73-3Relevant academic research and scientific papers
Synthesis of the Pentacyclic Core of Citreamicin η
Blumberg, Shawn,Martin, Stephen F.
, p. 790 - 793 (2017)
The citreamicins comprise a novel class of polycyclic xanthone natural products that have not yet yielded to total synthesis. A concise 11-step synthesis of the pentacyclic core of citreamicin η is now reported that features the use of a general approach for the synthesis of 1,4-dioxygenated xanthones. The synthesis also showcases improved techniques for effecting regioselective bromination of certain substituted phenols and coupling of acetylides with hindered ketones.
Toward the total synthesis of citreamicin η: Synthesis of the pentacyclic core and GAB-ring annelation model studies
Blumberg, Shawn,Martin, Stephen F.
, p. 4981 - 4993 (2018/05/23)
A short 11-step synthesis of the pentacyclic core of the polycyclic xanthone antibiotic citreamicin η has been completed. Although the basic approach was inspired by our previous explorations of polycyclic xanthone chemistry, the present report features some new insights into the Moore rearrangement and offers some improvements to our original methodology that include additions of aryllithiums to squarate esters, additions of cerium acetylides to hindered ketones utilizing PDA as an internal indicator, and the use of cyclic di-tert-butylsilyl (DTBS) ethers to protect electron-rich benzyl alcohols toward ionization under acidic conditions. We also developed an improved protocol for selective o-bromination of phenols utilizing N-bromosuccinimide (NBS) and tetramethylguanidine (TMG) that promises to be generally useful. Finally, we developed a modular approach for the synthesis of isoquinolones and dihydro-5H-oxazolo[3,2-b]isoquinoline-2,5(3H)-diones that features a novel sequence of alkoxycarbonylation, acetone arylation, transamidation.
INTERMEDIATES USEFUL FOR THE SYNTHESIS OF PYRROLOBENZODIAZEPINES
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Paragraph 0505; 0506, (2013/03/26)
A compound of formula (I): which is substantially free of any of the corresponding compound of formula (IB): methods of making such compounds, and the further transformation of such compounds.
INTERMEDIATES USEFUL FOR THE SYNTHESIS OF PYRROLOBENZODIAZEPINES
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Page/Page column 79-80, (2011/11/01)
A compound of formula (I): which is substantially free of any of the corresponding compound of formula (IB): methods of making such compounds, and the further transformation of such compounds.
Regioselective alkylation of catechols via Mitsunobu reactions
Wang, Xiaolong,Ju, Tingting,Li, Xiaodong,Cao, Xiaoping
experimental part, p. 2947 - 2949 (2011/02/22)
A mild and efficient Mitsunobu protocol for the regioselective alkylation of catechols such as 3,4-dihydroxybenzaldehyde and methyl 3,4-dihydroxybenzoate is described. The para-alkylation products could be easily prepared via the Mitsunobu reaction with high selectivity in moderate to good yields. Georg Thieme Verlag Stuttgart - New York.
Regioselective synthesis of syn disubstituted dibenzo-30-crown-10 ethers
Piatek, Piotr,Litwin, Aleksandra
experimental part, p. 2285 - 2289 (2009/07/11)
A practical and regioselective synthetic method for the synthesis of syn substituted dibenzo-30-crown-10 ethers is reported. This novel methodology is reported with the syntheses of dibenzo crown ethers bearing nitro, formyl and carbomethoxy groups. The s
IMIDAZOPYRAZINE TYROSINE KINASE INHIBITORS
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Page/Page column 188-189, (2008/06/13)
Compounds of the formula (I) and pharmaceutically acceptable salts thereof, wherein Q1 and R1 are defined herein, inhibit the IGF-1R enzyme and are useful for the treatment and/or prevention of various diseases and conditions that respond to treatment by inhibition of tyrosine kinases.
Benzylidene thiazolidinediones and their use as antimycotic agents
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Page/Page column 8, (2010/02/05)
A compound of formula I or a salt thereof wherein, A is O or S, X and Y independently represent O, CH2 and may be the same or different, Q is (CH2)m—CH(R1)—(CH2)n, R is OR6, NHR8, R1 is hydrogen, or optionally substituted alkyl, R2 and R3 are independently hydrogen, or specific substituents, provided that R2 and R3 are not both H, and R4 and R5 are hydrogen or specific substituents, m is 0-3; n is 0-2; are useful in the treatment of fungal infections.
Regioselective protection of the 4-hydroxyl of 3,4-dihydroxy-benzaldehyde
Plourde, Guy L.,Spaetzel, Randy R.
, p. 697 - 705 (2007/10/03)
The regioselective protection of the 4-hydroxyl group of 3,4-dihydroxy-benzaldehyde was accomplished with seven different protecting groups (benzyl, p-methoxybenzyl, o-nitrobenzyl, 2,6-dichlorobenzyl, 3,4-dichlorobenzyl, vinyl and propargyl) in yields ranging between 67-75percent.
