- Synthesis of the spiroketal core of integramycin
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A concise synthetic strategy towards the spiroketal core of the HIV-integrase inhibitor integramycin (1) was developed. The required ketone precursor was efficiently constructed from two simple and easily accessible subunits by means of a hydrozirconation/copper catalyzed acylation reaction. The effects of different protecting groups on the spiroketalization step were also investigated.
- Prusov, Evgeny V.
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- Biomimic transformation of resveratrol
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Resveratrol was treated with several kinds of peroxidases and inorganic reagents so as to prepare ε-viniferin. Among several inorganic reagents, which were investigated in this study, thallium(III) nitrate in methanol gave (±)-ε-viniferin in the yield of 68%. On the other hand, peroxidases did not lead to ε-viniferin, but some stilbenedimers such as pallidol, resveratrol trans-dehydrodimer, and leachianol F were obtained.
- Takaya, Yoshiaki,Terashima, Kenji,Ito, Junko,He, Yue-Hua,Tateoka, Maki,Yamaguchi, Naho,Niwa, Masatake
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- Scalable Total Synthesis of Piceatannol-3′-O-β-d-glucopyranoside and the 4′-Methoxy Congener Thereof: An Early Stage Glycosylation Strategy
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Scalable syntheses of piceatannol-3'-O-β-D-glucopyranoside and the 4'-methoxy congener thereof were achieved. This route features an early implemented Fischer-like glycosylation reaction, a regioselective iodination of phenolic glycoside under strongly acidic conditions, a highly telescoped route to access the styrene derivative, and a key Mizoroki.Heck reaction to render the desired coupled products in high overall yield.
- Chen, Lei,Li, Jianfeng,Wang, Xiaoting,Zhang, Rong-Ping
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- External-Radiation-Induced Local Hydroxylation Enables Remote Release of Functional Molecules in Tumors
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Radiation-induced cleavage for controlled release in vivo is yet to be established. We demonstrate the use of 3,5-dihydroxybenzyl carbamate (DHBC) as a masking group that is selectively and efficiently removed by external radiation in vitro and in vivo. D
- Duan, Dongban,Fu, Qunfeng,Li, Hongyu,Liu, Zhibo,Ma, Huimin,Shen, Siyong,Wang, Changlun
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supporting information
p. 21546 - 21552
(2020/09/07)
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- Unexpected O-alkylation and ester migration in phenolic 2,3-diaryl-2,3-dihydrobenzo[b]furans
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O-alkylation of 2-(4-methoxyphenyl)-5-hydroxy-3-[1,3-phenylene-bis(4- nitrobenzoate)]-2,3-dihydrobenzo[b]furan results in the unexpected hydrolysis of the nitrobenzoate esters, transfer of a 4-nitrobenzoic acid group to the 5-hydroxyl group and double alkylation of the newly formed 3,5-diphenol moiety. A range of alkyl halides can be used and give access to O-alkyl analogues of -viniferin.
- Tran, Henry,Dickson, Benjamin D.,Barker, David
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p. 2093 - 2096
(2013/04/23)
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- Synthesis of a tetrasubstituted tetrahydronaphthalene scaffold for α-helix mimicry via a MgBr2-catalyzed Friedel-Crafts epoxide cycloalkylation
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α-Helices are ubiquitous protein recognition elements that bind diverse biomolecular targets. The synthesis of a small molecule scaffold to present the side chains of an α-helix is described. The 1,3,5,7-tetrasubstituted 1,2,3,4-tetrahydronaphthalene scaf
- Naduthambi, Devan,Bhor, Santosh,Elbaum, Michael B.,Zondlo, Neal J.
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supporting information
p. 4892 - 4895
(2013/10/08)
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- Synthesis, electrochemistry and anticancer activity of novel ferrocenyl phenols prepared via azide-alkyne 1,3-cycloaddition reaction
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A series of monophenols and diphenols containing the ferrocene-C triazolyl and ferrocene-Ntriazolyl bond were prepared in a cycloaddition reaction of ethynylferrocene with aryl and benzyl azides and in a reaction of azidoferrocene with phenylacetylenes, respectively. The anticancer activity of the prepared compounds against hormone-dependent (MCF-7) and hormone-independent (HCC38) breast cancer cell lines was studied. The investigated compounds exhibited moderate anticancer activity against hormone-independent (IC50 ~ 15-48 μM) cancer cell line and low activity against hormone-dependent cancer cell line (IC50 ~ 84-98 μM).
- Plazuk, Damian,Rychlik, B?azej,B?auz, Andrzej,Domaga?a, S?awomir
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p. 102 - 112
(2012/09/07)
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- Synthesis of lipophilic N 9-benzylguanine derivatives
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Lipophilic N9-benzylguanine derivatives were synthesized from the arylalkylation of 2-N-acetylguanine with substituted benzyl bromides. Georg Thieme Verlag Stuttgart - New York.
- McCallum, Jeremy E. B.,Huston, Kenneth G.,McSweeney, Jacqueline M.,Rucker, Brandie G.
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scheme or table
p. 2871 - 2874
(2011/02/23)
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- Synthesis of supercritical carbon dioxide soluble perfluorinated dendrons for surface modification
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(Chemical Equation Presented) The rational design, synthesis, and characterization of a series of novel perfluorinated dendrons 14a,b, 25a,b, 26a,b, and 18 are described. The dendrimers were designed to have a thiol at the focal point for attachment to a gold surface to enable the fabrication of self-assembled monolayers (SAMs). Perfluorinated tails were attached to the periphery to provide solubility in supercritical carbon dioxide, and to increase the hydrophobicity and the stability of self-assembled monolayers formed. Mitsunobu reactions were utilized to provide high-yielding steps allowing large-scale production of the novel dendrimers.
- Luscombe, Christine K.,Proemmel, Steffen,Huck, Wilhelm T. S.,Holmes, Andrew B.,Fukushima, Hitoshi
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p. 5505 - 5513
(2008/02/09)
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- Vitamin D analogues
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The invention concerns novel bi-aromatic compounds having the formula: which are analogs of vitamin D, the process of preparing them, as well as their use in pharmaceutical compositions in human or veterinary medicine, particularly in dermatology, cancer treatment, treatment of auto-immune diseases, and in organ or tissue transplants. Cosmetic compositions and methods of use are also included.
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Page column 36
(2010/02/05)
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- Syntheses and radical scavenging activities of resveratrol derivatives
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Nine new resveratrol derivatives, having bromo, iodo, and fluoroethyl groups, were designed and synthesized. All compounds having free phenol groups showed good free radical scavenging activity. Among them, 2-bromoresveratrol 19 has a similar free radical scavenging activity to (+)-catechin.
- Lee, Hyun Jung,Seo, Jai Woong,Lee, Bong Ho,Chung, Kyoo-Hyun,Chi, Dae Yoon
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p. 463 - 466
(2007/10/03)
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- Synthesis of ardisinol II
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The first and also a concise synthesis of ardisinol II by two routes in excellent yields are described.
- Sun, Wei Yan,Zong, Qin,Gu, Rue Lin,Pan, Bai Chuan
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p. 1619 - 1622
(2007/10/03)
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- Total synthesis and structural elucidation of the antifungal agent papulacandin D
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Condensation of the aryllithium reagents, prepared from the bromides 10 and 11 and tert-butyllithium, with lactone 19 and acid-catalyzed spirocyclization gave the papulacandin spiroketals 14 and 15. Subsequent protection using di-tert-butylsilyl bis(trifluoromethanesulfonate) gave the diols 31 and 30. Isoleucine (37) was converted using a double Wittig reaction sequence and propargylation of the intermediate aldehyde 46 into the alkynol 47. Separation of the C-7 epimers of 47 was achieved using kinetic resolution via Sharpless epoxidation. Both alkynol epimers 53 and 57 were converted into the papulacandin side chain esters 65 and 66 using a hydrozirconation and palladium(0)-catalyzed coupling sequence. Comparisons of Mosher ester derivatives of 65 and 66 with the Mosher ester derivative of the natural papulacandin side chain and further degradation were consistent with the stereochemistry of the natural product being 7S,14S. Esterification of the spiroketals with the mixed anhydride 70 and global deprotection gave papulacandin D (1).
- Barrett, Anthony G. M.,Pena, Michael,Willardsen, J. Adam
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p. 1082 - 1100
(2007/10/03)
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- SYNTHESIS OF NATURAL POLYHYDROXYSTILBENES
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A synthesis of several natural polyhydroxystilbenes is described.
- Cardona, Luz,Fernandez, Isabel,Garcia, Begona,Pedro, Jose R.
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p. 2725 - 2730
(2007/10/02)
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