- Asymmetric Total Synthesis of TAN-1085 Facilitated by Pd-Catalyzed Atroposelective C-H Olefination
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Asymmetric total synthesis of TAN-1085 via Pd-catalyzed atroposelective C-H olefination is described. This synthesis features the gram-scale construction of axially chiral biaryls in an enantiopure form employing the readily available l-tert-leucine as th
- Fan, Jun,Yao, Qi-Jun,Liu, Yan-Hua,Liao, Gang,Zhang, Shuo,Shi, Bing-Feng
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supporting information
(2019/05/08)
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- Naphthoquinone derivative or a salt thereof as an active ingredient and horticultural fungicide containing (by machine translation)
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[A] a naphthoquinone derivative or salt thereof, or a salt thereof as an active ingredient horticultural fungicide containing said derivative, and use thereof. [Solution] the ingredient, represented by the following formula. [In the formula, R1 And R2 Is, for example, are each independently a hydrogen atom, a halogen, amino, substituted C1 - C6 The alkylcarbonyloxy groups such as shown, however, R1 And R2 Is, not simultaneously hydrogen atoms, R3 Is, for example, C1 - C6 Alkyl, C3 - C8 Cycloalkyl, C1 - C6 Alkoxy groups, R5 R6 N - shown as, R4 Is, a hydrogen atom or a halogen atom, here, R5 And R6 The, each independently hydrogen atom or C1 - C6 The alkyl groups, R5 And R6 The, the nitrogen atom to which they are attached together, may form a hetero ring, however, R5 And R6 The, are not simultaneously hydrogen atoms. ][Drawing] no (by machine translation)
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- Synthesis of Barleriaquinones-I & II
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Synthesis of two naturally occurring anthraquinones, Barleriaquinone-I (BQ-I) and Barleriaquinone-II (BQ-II) is achieved from commercially available naphthalene-1,5-diol. The anthraquinone core is constructed by utilizing simultaneous Heck and cross coupling reaction as the key step.
- Kumar Dende, Satheesh,Doddipalla, Raju,Reddy Nimmareddy, Rajashekar,Rapolu, Thirupathi,Babu Korupolu, Raghu,Leleti, Krishnakanth Reddy
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p. 1713 - 1720
(2019/05/15)
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- Novel heat shock protein 90 inhibitors suppress P-glycoprotein activity and overcome multidrug resistance in cancer cells
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Heat Shock Protein 90 (Hsp90) chaperone interacts with a broad range of client proteins involved in cancerogenesis and cancer progression. However, Hsp90 inhibitors were unsuccessful as anticancer agents due to their high toxicity, lack of selectivity against cancer cells and extrusion by membrane transporters responsible for multidrug resistance (MDR) such as P-glycoprotein (P-gp). Recognizing the potential of new compounds to inhibit P-gp function and/or expression is essential in the search for effective anticancer drugs. Eleven Hsp90 inhibitors containing an isoxazolonaphtoquinone core were synthesized and evaluated in two MDR models comprised of sensitive and corresponding resistant cancer cells with P-gp overexpression (human non-small cell lung carcinoma and colorectal adenocarcinoma). We investigated the effect of Hsp90 inhibitors on cell growth inhibition, P-gp activity and P-gp expression. Structure-activity relationship analysis was performed in respect to cell growth and P-gp inhibition. Compounds 5, 7, and 9 directly interacted with P-gp and inhibited its ATPase activity. Their potential P-gp binding site was identified by molecular docking studies. In addition, these compounds downregulated P-gp expression in MDR colorectal carcinoma cells, showed good relative selectivity towards cancer cells, while compound 5 reversed resistance to doxorubicin and paclitaxel in concentration-dependent manner. Therefore, compounds 5, 7 and 9 could be promising candidates for treating cancers with P-gp overexpression.
- Dini?, Jelena,Podolski-Reni?, Ana,Jovanovi?, Mirna,Musso, Loana,Tsakovska, Ivanka,Pajeva, Ilza,Dallavalle, Sabrina,Pe?i?, Milica
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- Novel methodology for the synthesis of the benzo[b]phenanthridine and 6H-dibenzo[c,h]chromen-6-one skeletons. Reactions of 2-naphthylbenzylamines and 2-naphthylbenzyl alcohols
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Novel syntheses of both the benzo[b]phenanthridine and the 6H-dibenzo[c,h]chromen-6-one motif are described. Reaction of (2-(3-bromo-1,4-dimethoxynaphthalen-2-yl)phenyl)methanamine with PIFA afforded benzo[b]phenanthridine-7,12-dione, while the related nonbrominated precursor, (2-(1,4,5-trimethoxynaphthalen-2-yl)phenyl)methanamine on treatment with PIFA, furnished the ortho-quinone 1-methoxybenzo[c]phenanthridine-11,12-dione. Unexpectedly, treatment of related oxygen analogs such as (2-(1,4-dimethoxynaphthalen-2-yl)phenyl)methanol with NBS under an O2atmosphere, afforded a chromenone, 12-methoxy-6H-dibenzo[c,h]chromen-6-one.
- Pradeep, Priyamvada,Ngwira, Kennedy J.,Reynolds, Chevonne,Rousseau, Amanda L.,Lemmerer, Andreas,Fernandes, Manuel A.,Johnson, Myron M.,de Koning, Charles B.
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p. 8417 - 8427
(2016/12/06)
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- A Divergent Enantioselective Strategy for the Synthesis of Griseusins
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The first enantioselective total synthesis of griseusin A, griseusin C, 4′-deacetyl-griseusin A, and two non-native counterparts in 11–14 steps is reported. This strategy highlights a key hydroxy-directed C H olefination of 1-methylene isochroman with an
- Zhang, Yinan,Ye, Qing,Wang, Xiachang,She, Qing-Bai,Thorson, Jon S.
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p. 11219 - 11222
(2016/07/06)
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- Copper-mediated oxidative trifluoromethylthiolation of quinones
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A novel copper-mediated oxidative trifluoromethylthiolation of quinones was developed. This protocol provided an efficient and practical approach to a series of trifluoromethylthiolated quinones.
- Li, Chao,Zhang, Ke,Xu, Xiu-Hua,Qing, Feng-Ling
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supporting information
p. 6273 - 6275
(2015/10/20)
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- Determining the absolute configuration of benzopyrenomycin by optical rotation, electronic circular dichroism, and population analysis of different conformations via DFT methods and experiments
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In this work, we have studied the absolute configuration of benzopyrenomycin using different density functional theory (DFT) methods, such as optical rotation (OR), electronic circular dichroism (ECD), and conformation distribution analysis for three kinds of Mosher esters at different levels, e.g., B3LYP/6-31G(d), B3LYP/6-311+G(d), and B3LYP/6-311++G(2d,p) in the gas phase and in solution, respectively. Careful investigations for different chiral Mosher esters using DFT theory exhibited the application conditions for certain chiral molecules in absolute configuration determination. Benzopyrenomycin possesses a unique benzo[a]pyrene-type skeleton and shows strong cytotoxicity against various tumor-cell lines.
- Li, Qing-Ming,Ren, Jie,Zhou, Bei-Dou,Bai, Bing,Liu, Xin-Chun,Wen, Meng-Liang,Zhu, Hua-Jie
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p. 3067 - 3074
(2013/03/29)
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- Total synthesis of jadomycins B, S, T, and ILEVS1080
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Sweetening up jadomycin A: The first total synthesis of jadomycins B, S, T, and ILEVS1080 has been achieved, featuring construction of the unique 8H-benz[b]oxazolo[3,3-f]phenanthridine skeleton by biomimetic condensation of a quinone aldehyde with amino acid sodium salts and elaboration of the glycosides by Mitsunobu condensation (see figure). Copyright
- Yang, Xiaoyu,Yu, Biao
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p. 8431 - 8434
(2013/07/19)
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- A diastereoselective oxa-pictet-spengler-based strategy for (+)-frenolicin B and epi -(+)-frenolicin B synthesis
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An efficient diastereoselective oxa-Pictet-Spengler reaction strategy was developed to construct benzoisochroman diastereomers. The utility of the reaction was demonstrated in the context of both the total synthesis of naturally occurring pyranonaphthoquinones (+)-frenolicin B and epi-(+)-frenolicin B as well as a range of frenolicin precursor analogs. The method is versatile and offers exquisite stereocontrol and, as such, offers a synthetic advance for the synthesis of pyranonaphthoquinone analogs.
- Zhang, Yinan,Wang, Xiachang,Sunkara, Manjula,Ye, Qing,Ponomereva, Larissa V.,She, Qing-Bai,Morris, Andrew J.,Thorson, Jon S.
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supporting information
p. 5566 - 5569
(2013/11/19)
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- Isoxazolo(aza)naphthoquinones: A new class of cytotoxic Hsp90 inhibitors
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A series of 3-aryl-naphtho[2,3-d]isoxazole-4,9-diones and some of their 6-aza analogues were synthesized and found to inhibit the heat shock protein 90 (Hsp90). The compounds were tested for their binding to Hsp90 and for their effects on Hsp90 client pro
- Bargiotti, Alberto,Musso, Loana,Dallavalle, Sabrina,Merlini, Lucio,Gallo, Grazia,Ciacci, Andrea,Giannini, Giuseppe,Cabri, Walter,Penco, Sergio,Vesci, Loredana,Castorina, Massimo,Milazzo, Ferdinando Maria,Cervoni, Maria Luisa,Barbarino, Marcella,Pisano, Claudio,Giommarelli, Chiara,Zuco, Valentina,De Cesare, Michelandrea,Zunino, Franco
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scheme or table
p. 64 - 75
(2012/07/30)
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- Synthesis study on marmycin A: Preparation of the C3′-desmethyl analogues
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(Chemical Equation Presented) Total synthesis of natural product marmycinAwas studied. An expeditious synthetic strategy for the key fragment 8-amino-3-methylbenz[a]anthraquinone (1) was established with decarboxylative alkylation, Pd(OAc)2-catalyzed cyclization, aromatization, and C - N coupling as the key steps. However, final assembly of marmycin A was hampered by the failure to obtain the carbohydrate fragment 2. Instead, a small library of desmethyl analogues of marmycinAwas prepared in moderate yields by using the InBr3-catalyzed C- and N-glycosidation reaction. The absolute configuration of these compounds was confirmed by comparison of their spectroscopic data with that reported for marmycin A, and by X-ray analysis.
- Ding, Chunyong,Tu, Shanghui,Li, Fuying,Wang, Yuanxiang,Yao, Qizheng,Hu, Wenxiang,Xie, Hua,Meng, Linghua,Zhang, Ao
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scheme or table
p. 6111 - 6119
(2009/12/26)
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- Efficient synthesis of (+)-kalafungin and (-)-nanaomycin D by asymmetric dihydroxylation, oxa-pictet-spengler cyclization, and H2SO 4-mediated isomerization
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The pyranonaphthoquinone antibiotics and antitumor agents (+)-kalafungin (1) and (-)-nanaomycin D (3 = ent-1) were synthesized from 1,5-napthalenediol (13) in 11 steps. Stereocontrol was high: 99.5 ee/93% diastereoselectivity for 1, 98.5% ee/94% diastereoselectivity for 3. Enantiocontrol was achieved by the asymmetric dihydroxylation of the β,γ-unsaturated ester 9. Diastereocontrol was realized in the final step by an almost complete epimerization in H2SO4.
- Fernandes, Rodney A.,Brückner, Reinhard
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p. 1281 - 1285
(2007/10/03)
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- Synthetic studies on kinamycin antibiotics: Synthesis of a trioxygenated benz[f]indenone and its Diels-Alder reaction to a kinamycin skeleton
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A benzo[b]fluorene skeleton such as 10, a basic four-ring system in the revised diazo structures 3 of kinamycin antibiotics, was synthesized by Diels-Alder reaction between dienophile 4,7,8-trioxygenated 1H-benz[f]inden-1-one 11 and Danishefsky-type diene 7. The indenone 11 was prepared by deoxygenation of 2,3-dihydro-1H-benz[f]inden-1-one 12 with the inexpensive 1 -hydroxy-1.2-benziodoxol-3(1H)-one 1-oxide (IBX) after modification of the known protocol. Indenone 12 in turn was obtained from naphthalene-1,5-diol (14) via an intramolecular Friedel-Crafts cyclization of naphthalene-2-propanoic acid 13 as a key step.
- Kitani, Yasuo,Morita, Akiko,Kumamoto, Takuya,Ishikawa, Tsutomu
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p. 1186 - 1195
(2007/10/03)
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- Oxidation of Hydroquinones and Hydroquinone Monomethyl Ethers to Quinones with tert-Butyl Hydroperoxide and Catalytic Amounts of Ceric Ammonium Nitrate (CAN)
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Mono- and bicyclic hydroquinones and hydroquinone monomethyl ethers 1, 2 are oxidized in 82-91% yield to the corresponding quinones using only 2 mol% of ceric ammonium nitrate (CAN) and 2.5 equivalents of tert-butyl hydroperoxide.
- Krohn, Karsten,Vitz, Juergen
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p. 825 - 827
(2007/10/03)
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- The Formal Oxidative Addition of Electron-Rich Transoid Dienes to Bromonaphthoquinones
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This work established the idea that a halogen atom, such as bromine, will act as a control element in the regiospecific formation of a new carbon-carbon bond.The addition of the electron-rich end of a transoid diene to a bromojuglone dervative occurred exclusively at the unsubstituted carbon of the quinone.Thus, 2,2-dimethyl-4-methoxy-6-methylene-1,3-dioxa-2-sila-4-cyclohexene (3) and either 2- or 3-bromo-5-hydroxy-1,4-naphthoquinone (1 or 2) afforded the adducts 19 or 20 in 57percent or 71percent yield.Similarly, 2,2-dimethyl-6-methylene-4-(trimethylsiloxy)-1,3-diox-4-ene (4) and 1 gave 21 in 77percent yield.
- Grunwell, John R.,Karipides, Anastas,Wigal, Carl T.,Heinzman, Stephen W.,Parlow, John,et al.
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- Synthetic Approaches to the Naphthyl-isoquinoline Alkaloids. Part 1. Dehydroancistrocladisine
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A synthesis of (+/-)-7-(4,5-dimethoxy-2-methyl-1-naphthyl)-6,8-dimethoxy-1,3-dimethylisoqinoline (dehydroancistrocladisine) 19, the racemic form of a degradation product of the unusual naphthylisoquinoline alkaloid ancistrocladisine 3, is recorded.The key
- Rizzacasa, Mark A.,Sargent, Melvyn V.
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p. 841 - 844
(2007/10/02)
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- Synthetic Approach to Aklavinone Using 2-Oxo-2H-pyran-5-carboxylate (Coumalate) Intermediates
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A novel approach for the preparation of aklavinone 5 is described in which the key step is the cycloaddition of a substituted coumalate with a ketene acetal to produce a masked A ring with the C and D rings attached.The 4-(arylmethyl)coumalate 53 was prepared from naphthalene-1,5-diol (6) by a seven step route involving as the key step the cyclocondensation of the methyl (arylmethyl)propiolate 52 with methyl 3-oxopentanoate 10.Cycloaddition of 53 with dimethyl ketene acetal 12 produced the potential A-ring precursor 67, which could not be cleanly reduced, thereby ending this scheme.The preparation of functionalized 4,6-dialkylpyrone-5-carboxylates and their use in the synthesis of bicyclic lactones and substituted benzoates via cycloaddition reactions are also described.
- Jung, Michael E.,Hagenah, Jeffrey A.
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p. 1889 - 1902
(2007/10/02)
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- Regiospecific synthesis of bromojuglone derivatives
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A large yield highly regiospecific one step procedure for the synthesis of 2- and 3-bromo-5-acetoxy-1,4-naphthoquinone has been achieved from the reaction between N-bromosuccin-imide and 1,5- and 1,8-diacetoxynaphthalene, respectively.
- Heinzman, Stephen W.,Grunwell, John R.
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p. 4305 - 4308
(2007/10/02)
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