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The N‐amino‐ribono‐1,5‐lactam 4 was prepared in two high‐yielding steps from the known methanesulfonate 2 . Oxidation of 4 with t‐BuOCl in the presence of 2,6‐lutidine afforded the tetrazene 6 (63%). Oxidation with MnO2 gave the deaminated lactam 7 (40%), which was also obtained, together with the lactone 8 , upon oxidation of 4 with PhSeO2H. Oxidation with Mn(OAc)3/Cu(OAc)2 provided the lactam 7 as the major and the dimer 9 as the minor product. Oxidation of 4 with 3 equiv. of Pb(OAc)4 in toluene at room temperature gave two cyclopentanes, viz. the acetoxy epoxide 10 and the diazo ketone 11 in a combined yield of 78%. Oxidation with Pb(OBz)4 provided 11 and the crystalline benzoyloxy epoxide 12 . The crystal structure of 12 was established by X‐ray analysis. The N‐amino‐glyconolactams 41, 46 , and 51 were prepared similarly to 4 . Their oxidation with Pb(OAc)4 provided the diazo ketones 56, 57 , and 58 as the only isolable products. Oxidation of the N‐amino‐mannono‐1,5‐lactam 55 with Pb(OAc)4 in the presence of DMSO gave the sulfoximine 59 . Mannostatin A, a strong α‐mannosidase inhibitor, was synthesized from the acetoxy epoxide 10 (obtained in 48% from 4 ) in seven steps and in an overall yield of 45%. 相似文献
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Nataliia V. Shymanska Il Hwan An Prof. Joshua G. Pierce 《Angewandte Chemie (International ed. in English)》2014,53(21):5401-5404
A five‐step total synthesis of the marine natural product synoxazolidinone A was achieved through a diastereoselective imine acylation/cyclization cascade. Synoxazolidinone B and a series of analogues were also prepared to explore the potential of these 4‐oxazolidinone natural products as antimicrobial agents. These studies confirmed the importance of the chlorine substituent for antimicrobial activity and revealed simplified dichloro derivatives that are equally potent against several bacterial strains. 相似文献
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Yong Ni Dr. Tullimilli Y. Gopalakrishna Dr. Hoa Phan Dr. Tun Seng Herng Shaofei Wu Yi Han Prof. Jun Ding Prof. Jishan Wu 《Angewandte Chemie (International ed. in English)》2018,57(31):9697-9701
Peri‐acenes are good model compounds for zigzag graphene nanoribbons, but their synthesis is extremely challenging owing to their intrinsic open‐shell diradical character. Now, the successful synthesis and isolation of a stable peri‐tetracene derivative PT‐2ClPh is reported; four 2,6‐dichlorophenyl groups are attached onto the most reactive sites along the zigzag edges. The structure was confirmed by X‐ray crystallographic analysis and its electronic properties were systematically investigated by both experiments and theoretical calculations. It exhibits an open‐shell singlet ground state with a moderate diradical character (y0=51.5 % by calculation) and a small singlet–triplet gap (ΔES‐T=?2.5 kcal mol?1 by SQUID measurement). It displays global aromatic character, which is different from the smaller‐size bisanthene analogue BA‐CF3 . 相似文献
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Youai Qiu Jing Zhou Prof. Dr. Chunling Fu Prof. Dr. Shengming Ma 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(45):14589-14593
[IPrAuCl]/AgSbF6‐catalyzed cyclization of the readily available 4‐benzoxyl‐1‐(indol‐2‐yl)‐2‐alkynols occurred smoothly in 1,2‐dichloroethane (DCE) in the presence of 4 Å MS to form a series of differently polysubstituted 2‐oxygenated carbazole derivatives efficiently. Based on mechanistic study, a possible mechanism involving 1,3‐migration of a benzoate group to form the allene, Au+‐mediated cyclization–elimination to form a gold–carbene intermediate, and subsequent highly selective 1,2‐migration has been proposed for the formation of carbazoles. Highly selective 1,2‐migration referring to the two substituents R3 and R4 (R4=H, alkyl, and aryl group) was observed: (1) In the presence of both H and alkyl groups, 1,2‐hydrogen migration is exclusive; (2) in the presence of a methyl group (R3), propyl, isopropyl, 4‐methylphenyl, and 4‐chlorophenyl groups (R4) migrate exclusively. Finally, the first total synthesis of the recently isolated naturally occurring carbazole alkaloid karapinchamine A in 5.2 g scale has been realized in 6 steps from commercially available chemicals without need for any protection–deprotection. 相似文献
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A Concise and Versatile Synthesis of Alkaloids from Kopsia tenuis: Total Synthesis of (±)‐Lundurine A and B 下载免费PDF全文
Prof. Shigeru Arai Masaya Nakajima Prof. Atsushi Nishida 《Angewandte Chemie (International ed. in English)》2014,53(22):5569-5572
A total synthesis of (±)‐lundurines A and B is described. These natural products have a unique hexacyclic skeleton which includes a cyclopropane‐fused indoline. A stereospecific construction of the pentasubstituted cyclopropane core was achieved, by radical cyclization using SmI2, with perfect stereoselectivity. Cyclizations to give seven‐ and five‐membered heterocycles, under palladium and ruthenium catalysis, respectively, accomplished the total syntheses. The late‐stage construction of the F ring by ring‐closing metathesis enabled access to the title compounds from a spiroindoline intermediate which is a common structure of other kopsia alkaloids. 相似文献
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Divergent Solid‐Phase Synthesis of Natural Product‐Inspired Bipartite Cyclodepsipeptides: Total Synthesis of Seragamide A 下载免费PDF全文
Prof. Dr. Hans‐Dieter Arndt Dr. Stefano Rizzo M. Sc. Christina Nöcker Dr. Vijay N. Wakchaure Dr. Lech‐Gustav Milroy B. Sc. Vanessa Bieker Dr. Abram Calderon Dr. Tuyen T. N. Tran Dr. Silke Brand Dr. Leif Dehmelt Prof. Dr. Herbert Waldmann 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(14):5311-5316
Macrocyclic natural products (NPs) and analogues thereof often show high affinity, selectivity, and metabolic stability, and methods for the synthesis of NP‐like macrocycle collections are of major current interest. We report an efficient solid‐phase/cyclorelease method for the synthesis of a collection of macrocyclic depsipeptides with bipartite peptide/polyketide structure inspired by the very potent F‐actin stabilizing depsipeptides of the jasplakinolide/geodiamolide class. The method includes the assembly of an acyclic precursor chain on a polymeric carrier, terminated by olefins that constitute complementary fragments of the polyketide section and cyclization by means of a relay‐ring‐closing metathesis (RRCM). The method was validated in the first total synthesis of the actin‐stabilizing cyclodepsipeptide seragamide A and the synthesis of a collection of structurally diverse bipartite depsipeptides. 相似文献
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《Journal of heterocyclic chemistry》2017,54(1):27-34
In the current scenario for continuous requirement of better drugs, medicinal chemists must visage the challenging task of preparing novel patentable compounds, combining high activity and selectivity, good drug‐likeness, and pharmacokinetic properties. There is an acute need of new molecules in both lead identification and lead optimization. Chemists thoroughly scrutinize ways to simplify synthetic protocols using green chemistry approaches, for example, microwaves. Reduction in the reaction time by the use of microwaves has emerged as a promising method for bringing out new leads in organic synthesis. Among the azaheterocyclic systems, synthesis of pyrrole moiety has been a highly attractive and an inspiring proposition. It has been found to be an inbuilt pharmacophore of various momentous pharmacologically active compounds in medicinal chemistry. This article outlines the basic principles of microwave technology and its use in the synthesis of pyrrole derivatives wherein this technology has made a tremendous impact. 相似文献
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A new compound: octaiodoanthraquinone (9,10) was synthesized from anthracene by a periodination process under the catalysis of mercury ions at 200?250 °C. This new compound was also synthesized from anthraquinone (9,10) via a similar process, which verified the mercury‐catalyzed mechanism involved in the synthesis of octaiodoanthraquinone (9,10) from anthracene. 相似文献