32384-42-2Relevant articles and documents
[2+2] Photoadditions with chiral 2,5-cyclohexadienone synthons
Lange, Gordon L.,Humber, Craig C.,Manthorpe, Jeffrey M.
, p. 1355 - 1362 (2002)
Three chiral 2,5-cyclohexadienone synthons bearing different chiral auxiliaries were examined in [2+2] photoadditions with cyclopentene. Regeneration of the 'masked' double bond in the adducts resulted in the preparation of optically active 5-4-6 adducts. The enantiomeric purity of each adduct was found to be >95% using comparative 13C NMR analysis of the appropriate ketals. The asymmetry induced in the cycloaddition step of our methodology indicated that the facial selectivity was directly correlated to the degree of steric bulk of the chiral auxiliary on the synthon.
Parallel synthesis and biological evolution of quinic acid derivatives as immuno-suppressing agents against T-cell receptors
Huang, Chih-Yu,Chen, Li-Hsun,Huang, Hsuan-Yu,Kao, Feng-Sheng,Lee, Yun-Ta,Selvaraju, Manikandan,Sun, Chung-Ming,Chen, Hueih-Min
, p. 50801 - 50806 (2015)
A simple protocol for the synthesis of quinic acid derivatives was established and their biological evolution against T-cells is studied. Results showed that one of the derivatives, Cyn-1324, has low toxicity on T-cells and a high effect on reducing Signal 2 of T-cell immune responses. In vitro binding measurements of atomic force spectroscopy further indicated that the blocking effect of Cyn-1324 between CD28 and CD80 was about 31 ± 4%. In vivo animal tests also confirmed that Cyn-1324 can reduce the allergic responses from ovalbumin-induced mice with little toxicity. Based on these observations, Cyn-1324 can be a mild immuno-suppressive candidate for future drug development.
Asymmetric Total Synthesis of (-)-Guignardones A and B
Gong, Jianxian,Yan, Zhiming,Yang, Zhen,Zhao, Chunbo
, (2020)
The asymmetric total synthesis of (-)-guignardones A (2) and B (1) has been accomplished. The highly oxidized 6-oxabicyclo[3.2.1]octane core was constructed from d-quinic acid via substitution/desulfurization reaction with thiophenol to forge the bridged ring scaffold, and a Pummerer rearrangement and 1,4-addition/elimination sequence was employed to install the β-carbonyl group at the congested C-1 position. A late-stage Knoevenagel condensation-6π-electrocyclization and directed hydrogenation formed (-)-guignardone B (1), which was subjected to dehydration to furnish (-)-guignardone A (2).
Facile synthesis of the cyclohexane fragment of enacloxins, a series of antibiotics isolated from Frateuria sp. W-315
Saito, Aki,Igarashi, Wataru,Furukawa, Hiroyuki,Yamada, Teiko,Kuwahara, Shigefumi,Kiyota, Hiromasa
, p. 766 - 769 (2014)
An efficient and good yield synthesis of the cyclohexane moiety of enacyloxins, a series of antibiotics isolated from Frateuria sp. W-315, was achieved from D-quinic acid using a successive Barton - McCombie deoxygenation.
Total syntheses of aminomethyl-C-dideoxyglycopyranosides and their quinamides
Gremyachinskiy, Dmitriy E.,Samoshin, Vyacheslav V.,Gross, Paul H.
, p. 6587 - 6590 (2003)
Lewis acid promoted cyclization of homoallylic alcohol 1 with acetal 2 gave 4-chloro-2-phthalimidomethyl-6-methyltetrahydropyrans. Their dehydrochlorination produced two regioisomeric dihydropyrans. Subsequent cis- and trans-dihydroxylation gave four race
Sulfamate-tethered aza-Wacker approach towards analogs of Bactobolin A
Nagamalla, Someshwar,Johnson, David K.,Sathyamoorthi, Shyam
, p. 1348 - 1357 (2021/04/09)
Here, we describe an approach towards analogs of the potent antibiotic Bactobolin A. Sulfamate-tethered aza-Wacker cyclization reactions furnish key synthons, which we envision can be elaborated into analogs of Bactobolin A. Docking studies show that the
Synthetic Studies of the Rubellin Natural Products: Development of a Stereoselective Strategy and Total Synthesis of (+)-Rubellin C
Gartman, Jackson A.,Tambar, Uttam K.
, p. 11237 - 11262 (2021/08/16)
This manuscript describes our studies of the class of natural products known as the rubellins, culminating in the total synthesis of (+)-rubellin C. These anthraquinone-based natural products contain a variety of stereochemical and architectural motifs, including a 6-5-6-fused ring system, 5 stereogenic centers, and a central quaternary center. Herein, we report our development of a strategy to target the stereochemically dense core and anthraquinone nucleus, including approaches such as a bifunctional allylboron and vinyl triflate reagent, an anthraquinone benzylic metalation strategy, and a late-stage anthraquinone introduction strategy. Our studies culminate in a successful route to highly functionalized anthraquinone-based natural product scaffolds and a stereoselective total synthesis of (+)-rubellin C. These strategies and outcomes will aid in synthetic planning toward anthraquinone-based natural products of high interest.
A concise synthesis of carbasugars isolated from Streptomyces lincolnensis
Holmstedt, Suvi,Candeias, Nuno R.
, (2020/07/03)
(?)-Quinic acid was used as a starting material in the hemisynthesis of two epimeric carbasugars isolated from Streptomyces lincolnensis. Previous 10–12 steps syntheses for the carbasugars have been herein shortened to 4–6 steps by using quinic acid as a
Total Synthesis of (+)-Rubellin C
Gartman, Jackson A.,Tambar, Uttam K.
supporting information, p. 9145 - 9150 (2020/08/24)
The rubellins are a family of stereochemically complex anthraquinoid heterodimers containing an unprecedented chemical scaffold. Although the rubellins have been known for over three decades, no total synthesis has been achieved since their discovery. The
Process for synthesizing oseltamivir sulfonate from quinic acid
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Paragraph 0009; 0023-0025; 0033-0035; 0043-0045, (2021/01/04)
The invention discloses a process for synthesizing oseltamivir sulfonate from quinic acid. The process specifically comprises the following steps of: S1, adding quinic acid and ethyl acetate into a round-bottom flask, and adding p-toluenesulfonic acid and 2, 2-dimethoxypropane, carrying out reaction to obtain a brown solid 2; S2, adding the brown solid 2 and dichloromethane into the round-bottom flask, dropwise adding methanesulfonyl chloride and triethylamine into the round-bottom flask while performing stirring, and carrying out reaction to obtain an intermediate 3; S3, adding the obtained intermediate 3 into a three-neck flask, adding ethanol and sodium ethoxide for reaction, and removing the dichloromethane after finishing the reaction to obtain an intermediate 4; and S4, adding the intermediate 4 and dichloromethane into the round-bottom flask, dropwise adding the methanesulfonyl chloride and triethylamine into the round-bottom flask while performing stirring, extracting a reaction solution with dichloromethane and water after finishing the reaction, concentrating an obtained organic phase under reduced pressure, adding methanol for crystallization, and performing filtering toobtain a white crystal 5, namely oseltamivir sulfonate.
