排序方式: 共有16条查询结果,搜索用时 15 毫秒
1.
Hodgson DM Kirton EH Miles SM Norsikian SL Reynolds NJ Coote SJ 《Organic & biomolecular chemistry》2005,3(10):1893-1904
Organolithium-induced deprotonation of terminal epoxides in the presence of appropriate diamine ligands allows trapping with a range of electrophiles, yielding functionalised di- and tri-substituted epoxides in good yields and with control of stereochemistry at the epoxide. 相似文献
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From Enantiopure Hydroxyaldehydes to Complex Heterocyclic Scaffolds: Development of Domino Petasis/Diels–Alder and Cross‐Metathesis/Michael Addition Reactions 下载免费PDF全文
Dr. Alexandre Cannillo Dr. Stéphanie Norsikian Dr. Marie‐Elise Tran Huu Dau Dr. Pascal Retailleau Dr. Bogdan I. Iorga Prof. Jean‐Marie Beau 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(38):12133-12143
One‐step assembly of hexahydroisoindole scaffolds by a sequence that combines the Petasis (borono‐Mannich) and Diels–Alder reactions is described. The unique selectivity observed experimentally was confirmed by quantum calculations. The current method is applicable to a broad range of substrates, including free sugars, and holds significant potential to efficiently and stereoselectively build new heterocyclic structures. This easy and fast entry to functionalized polycyclic compounds can be pursued by further transformations, for example, additional ring closure by a cross‐metathesis/Michael addition domino sequence. 相似文献
3.
Georgiana Surpateanu Jean-François Soulé Jean-Marie Beau Stéphanie Norsikian Bogdan I. Iorga 《Journal of carbohydrate chemistry》2013,32(2):114-129
The conformational flexibility of two glycal-type neuraminidase inhibitors has been studied, using several molecular modeling techniques. In agreement with the experimental data available, an intramolecular hydrogen bond, representing a key structural feature that controls the conformer distribution in solution, has been identified. The contribution of each substituent to the overall equilibrium was evaluated using simplified derivatives. Additionally, four methods for estimating NMR coupling constants from dihedral angles were evaluated and the Haasnoot method was found to be appropriate for this class of sugars. These results should allow a better understanding of the structural parameters governing physico-chemical properties of glycal-like compounds. Supplemental materials are available for this article. Go to the publisher's online edition of Journal of Carbohydrate Chemistry to view the free supplemental file. 相似文献
4.
Dr. Cédric Tresse Dr. Marc François-Heude Vincent Servajean Rubal Ravinder Clémence Lesieur Lucie Geiben Dr. Louis Jeanne-Julien Vincent Steinmetz Dr. Pascal Retailleau Dr. Emmanuel Roulland Prof. Dr. Jean-Marie Beau Dr. Stéphanie Norsikian 《Chemistry (Weinheim an der Bergstrasse, Germany)》2021,27(16):5230-5239
We give a full account of the total synthesis of tiacumicin B (Tcn-B), a natural glycosylated macrolide with remarkable antibiotic properties. Our strategy is based on our experience with the synthesis of the tiacumicin B aglycone and on unique 1,2-cis-glycosylation steps. We used sulfoxide anomeric leaving-groups in combination with a remote 3-O-picoloyl group on the donors that allowed highly β-selective rhamnosylation and noviosylation that rely on H-bond-mediated aglycone delivery. The rhamnosylated C1–C3 fragment was anchored to the C4–C19 aglycone fragment by a Suzuki–Miyaura cross-coupling. Ring-size-selective Shiina macrolactonization provided a semiglycosylated aglycone that was engaged directly in the noviolysation step with a virtually total β-selectivity. Finally, a novel deprotection method was devised for the removal of a 2-naphthylmethyl ether on a phenol, and efficient removal of all the protecting groups provided synthetic tiacumicin B. 相似文献
5.
Iron(III) chloride hexahydrate promotes a cascade of transformations on a Petasis condensation product that sets up the right dihydropyran precursors of valuable Relenza congeners. 相似文献
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Dr. Stéphanie Norsikian Dr. Cedric Tresse Dr. Marc François-Eude Dr. Louis Jeanne-Julien Dr. Guillaume Masson Vincent Servajean Dr. Grégory Genta-Jouve Prof. Jean-Marie Beau Dr. Emmanuel Roulland 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2020,132(16):6674-6678
A total synthesis of tiacumicin B, a natural macrolide whose remarkable antibiotic properties are used to treat severe intestinal infections, is reported. The strategy is in part based on the prior synthesis of the tiacumicin B aglycone, and on the decisive use of sulfoxides as anomeric leaving groups in hydrogen-bond-mediated aglycone delivery (HAD). This new HAD variant permitted highly β-selective rhamnosylation and noviosylation. To increase convergence, the rhamnosylated C1–C3 fragment thus obtained was anchored to the C4–C19 aglycone fragment by adapting the Suzuki–Miyaura cross-coupling used for the aglycone synthesis. Ring-size-selective macrolactonization provided a compound engaged directly in the noviolysation step with virtually total β selectivity. The final efficient removal of all the protecting groups provided synthetic tiacumicin B. 相似文献
8.
An unprecedented intramolecular Petasis condensation provides a novel approach to biologically important conduramines. The compounds are produced with an exclusive anti stereoselectivity for the newly created β-amino alcohol motif. The stereochemical outcome of the reaction is opposite to the one usually observed in the intermolecular reaction. 相似文献
9.
Stphanie Norsikian Cedric Tresse Marc Franois‐Eude Louis Jeanne‐Julien Guillaume Masson Vincent Servajean Grgory Genta‐Jouve Jean‐Marie Beau Emmanuel Roulland 《Angewandte Chemie (International ed. in English)》2020,59(16):6612-6616
A total synthesis of tiacumicin B, a natural macrolide whose remarkable antibiotic properties are used to treat severe intestinal infections, is reported. The strategy is in part based on the prior synthesis of the tiacumicin B aglycone, and on the decisive use of sulfoxides as anomeric leaving groups in hydrogen‐bond‐mediated aglycone delivery (HAD). This new HAD variant permitted highly β‐selective rhamnosylation and noviosylation. To increase convergence, the rhamnosylated C1–C3 fragment thus obtained was anchored to the C4–C19 aglycone fragment by adapting the Suzuki–Miyaura cross‐coupling used for the aglycone synthesis. Ring‐size‐selective macrolactonization provided a compound engaged directly in the noviolysation step with virtually total β selectivity. The final efficient removal of all the protecting groups provided synthetic tiacumicin B. 相似文献
10.
SL Mironov E Skorova G Taschenberger N Hartelt VO Nikolaev MJ Lohse S Kügler 《BMC neuroscience》2009,10(1):29-11