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Total synthesis of marine-derived azole resistant antifungal agent (-)-melearoride A and antibiotic (-)-PF1163B 海洋衍生抗真菌药(-)-melearoride A和抗生素(-)- pf1163b的全合成
IF 2.5
SynOpen Pub Date : 2022-09-14 DOI: 10.1055/a-1942-6969
Srihari Pabbaraja, Bharath Yasam
{"title":"Total synthesis of marine-derived azole resistant antifungal agent (-)-melearoride A and antibiotic (-)-PF1163B","authors":"Srihari Pabbaraja, Bharath Yasam","doi":"10.1055/a-1942-6969","DOIUrl":"https://doi.org/10.1055/a-1942-6969","url":null,"abstract":"A flexible stereoselective and convergent cum divergent approach to the synthesis of two 13-membered macrolides through a common skeleton present in their structure is described in two different routes, with good overall yield. The key synthetic reactions utilized include Keck allylation, Evans asymmetric methylation, Grubbs metathesis and Julia-Kocienski olefination reaction.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":" ","pages":""},"PeriodicalIF":2.5,"publicationDate":"2022-09-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43659489","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
Stereoselective Synthesis of Euscapholide and Tetraketide via Prins Cyclisation and Ring-Closing Metathesis Prins环化和闭环复分解立体选择性合成环己内酯和四酮
IF 2.5
SynOpen Pub Date : 2022-09-12 DOI: 10.1055/s-0042-1751381
D. Biradar, Y. Mane, B. S. Subba Reddy
{"title":"Stereoselective Synthesis of Euscapholide and Tetraketide via Prins Cyclisation and Ring-Closing Metathesis","authors":"D. Biradar, Y. Mane, B. S. Subba Reddy","doi":"10.1055/s-0042-1751381","DOIUrl":"https://doi.org/10.1055/s-0042-1751381","url":null,"abstract":"A concise and diastereoselective total synthesis of tetraketide and euscapholide is described in ten steps in 10.6% overall yield from acetaldehyde and (S)-pent-4-ene-1,2-diol. Jacobsen hydrolytic kinetic­ resolution, Prins cyclization, ring-closing metathesis and oxa-Michael­ addition reactions are the key steps involved in the synthesis.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"06 1","pages":"312 - 318"},"PeriodicalIF":2.5,"publicationDate":"2022-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41517644","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Zinc acetate catalyzed stereoselective 1,2 trans glycosylation using glycosyl chlorides 乙酸锌催化糖基氯化物立体选择性1,2反式糖基化反应
IF 2.5
SynOpen Pub Date : 2022-09-12 DOI: 10.1055/a-1941-3801
Mohammad Saif Ali, Ramesh P.I, Subhash Ghosh, M. Tatina
{"title":"Zinc acetate catalyzed stereoselective 1,2 trans glycosylation using glycosyl chlorides","authors":"Mohammad Saif Ali, Ramesh P.I, Subhash Ghosh, M. Tatina","doi":"10.1055/a-1941-3801","DOIUrl":"https://doi.org/10.1055/a-1941-3801","url":null,"abstract":"We report the strategy for the stereoselective synthesis of 1,2-trans glycosides in the absence of NGP (neighboring group participation). Present protocol for the selective glycosylation mainly rely on catalyst control rather than protecting group selection. Using this protocol, several glycosides were prepared. Cost effective zinc acetate was found to be the best catalyst that provided desired 1,2-trans glycosides from glucose and mannose derived glycosyl halides at room temperature unlike traditional cryogenic conditions.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":"1 1","pages":""},"PeriodicalIF":2.5,"publicationDate":"2022-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41415840","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
Palladium-Catalysed Reductive Aminocarbonylation of Aryl Bromides and Iodides with Nitroarenes 钯催化芳基溴和碘与硝基芳烃的还原氨基羰基化反应
IF 2.5
SynOpen Pub Date : 2022-09-01 DOI: 10.1055/s-0040-1720041
Paseka T. Moshapo, Blessing D. Mkhonazi, Euphrent M. Mabila
{"title":"Palladium-Catalysed Reductive Aminocarbonylation of Aryl Bromides and Iodides with Nitroarenes","authors":"Paseka T. Moshapo, Blessing D. Mkhonazi, Euphrent M. Mabila","doi":"10.1055/s-0040-1720041","DOIUrl":"https://doi.org/10.1055/s-0040-1720041","url":null,"abstract":"Amide functional groups are a structural feature in a vast array of beneficial organic molecules. This has resulted in a surge in new methodologies developed to enable access to this functional group using a broad range of coupling partners. Herein, we report a palladium-catalysed reductive aminocarbonylation of aryl bromides and iodides with nitroarenes to afford the respective amide products. The developed protocol employs Mo(CO)6 as a carbonyl source and a combination of Zn and TMSCl as co-reducing agents. For most substrates, the anticipated amide products were obtained in modest to high amide product yields.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":" ","pages":""},"PeriodicalIF":2.5,"publicationDate":"2022-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46480411","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Approaches to the total synthesis of conduramines: A Review 孔杜拉明的全合成方法综述
IF 2.5
SynOpen Pub Date : 2022-08-29 DOI: 10.1055/a-1933-0602
V. Batchu, H. Bharathkumar, J. S. Krishna, Banothu Surender
{"title":"Approaches to the total synthesis of conduramines: A Review","authors":"V. Batchu, H. Bharathkumar, J. S. Krishna, Banothu Surender","doi":"10.1055/a-1933-0602","DOIUrl":"https://doi.org/10.1055/a-1933-0602","url":null,"abstract":"This review reports on the total synthesis of conduramines, which are formally derived from conduritols, these molecules are mainly contains trihydroxy aminocyclohexene core. Analysis of the different strategies developed to prepare these aminocyclohexene triols and their derivatives has been carried out with special attention paid to the methods employed for the insertion of chiral amine moiety.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":" ","pages":""},"PeriodicalIF":2.5,"publicationDate":"2022-08-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44724715","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
Transition Metal-Catalyzed Remote C–H Bond Functionalization of Cyclic Amines 过渡金属催化环胺的远端C-H键功能化
IF 2.5
SynOpen Pub Date : 2022-08-24 DOI: 10.1055/a-1929-9789
Weijie Chen, Xiaoyu Yang, Xiaobei Cao
{"title":"Transition Metal-Catalyzed Remote C–H Bond Functionalization of Cyclic Amines","authors":"Weijie Chen, Xiaoyu Yang, Xiaobei Cao","doi":"10.1055/a-1929-9789","DOIUrl":"https://doi.org/10.1055/a-1929-9789","url":null,"abstract":"C–H bond functionalization is one of the most effective strategies for the rapid synthesis of cyclic amines containing substituents in the ring, which are core structures of many bioactive molecules. It is, however, much more challenging to perform this strategy on remote C–H bonds compared to α-C–H bonds of cyclic amines. This graphical review aims to provide a concise overview on transition metal-catalyzed methods for the remote C–H bond functionalization of cyclic amines. Examples are categorized and demonstrated according to mechanistic pathways that initiate the reaction of cyclic amine substrates. Selected substrate scope and detailed reaction mechanisms are given when necessary.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":" ","pages":""},"PeriodicalIF":2.5,"publicationDate":"2022-08-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48153677","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
Organo-photocatalytic Synthesis of Functionalized Pyrroles from 2H-Azirines and α-Substituted Nitroalkenes 由2h -氮嘧啶和α-取代硝基烯有机光催化合成功能化吡咯
IF 2.5
SynOpen Pub Date : 2022-08-23 DOI: 10.1055/s-0042-1751360
N. Rastogi, L. Devi, Poornima Mishra, Ayush Pokhriyal
{"title":"Organo-photocatalytic Synthesis of Functionalized Pyrroles from 2H-Azirines and α-Substituted Nitroalkenes","authors":"N. Rastogi, L. Devi, Poornima Mishra, Ayush Pokhriyal","doi":"10.1055/s-0042-1751360","DOIUrl":"https://doi.org/10.1055/s-0042-1751360","url":null,"abstract":"An efficient organo-photocatalytic method for the synthesis of tetrasubstituted pyrroles bearing a ketone, ester, alcohol, or nitro group at the 3-position has been developed. The reaction involves visible-light-mediated formal [3+2] dipolar cycloaddition between 2H-azirines and α-substituted nitroalkenes followed by a denitration or debromination sequence. The notable features of the protocol are excellent regioselectivity, wide substrate scope, and high yields of the products.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":" ","pages":""},"PeriodicalIF":2.5,"publicationDate":"2022-08-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44193674","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
Baeyer–Villiger Monooxygenases (BVMOs) as Biocatalysts Baeyer-Villiger单加氧酶(BVMOs)作为生物催化剂
IF 2.5
SynOpen Pub Date : 2022-08-17 DOI: 10.1055/s-0042-1751359
P. Chawla, Chandrakant Sahu
{"title":"Baeyer–Villiger Monooxygenases (BVMOs) as Biocatalysts","authors":"P. Chawla, Chandrakant Sahu","doi":"10.1055/s-0042-1751359","DOIUrl":"https://doi.org/10.1055/s-0042-1751359","url":null,"abstract":"Natural or artificial enzymes are used in biocatalytic processes to produce high-value fine chemicals, most notably chiral pharmaceutical intermediates. On the other hand, there are few instances of the enzymatic production of bulk compounds.1 In particular production of polymer precursors such as -caprolactone, currently obtained from cyclohexanone utilizing peracetic acid; where Baeyer–Villiger monooxygenases (BVMOs) are potential alternative catalysts to carry out the reaction under much milder conditions.2 Bulk manufacturing of feedstock chemicals utilizing biocatalysts such as BVMO has yet to be accomplished due to a number of reasons.3 The versatility of BVMOs is highlighted in this Spotlight, along with various instances of how protein engineering has been employed to circumvent some of the disadvantages of BVMO use. BVMOs are flavin-reliant enzymes that utilize molecular oxygen and NAD(P)H to catalyze a number of oxidation processes, including Baeyer–Villiger oxidations (Table 1).4,5 The genes to encode them were discovered at the beginning of this century.6 Even though the biochemical reason for the retention of these residues was unclear until recently, the sequence pattern has shown to be quite useful for mining genomes for new BVMOs.7 Although the genomes of higher animals and plants do not include any type I BVMOs, bacteria are rich in BVMOs, with one BVMO per genome on average.8 These enzymes are notably common among the Actinomycetes, making them an intriguing source of new BVMOs.9 Fungal genomes are also rather rich in BVMOs but have not yet been fully investigated.10 The crucial functions that BVMOs play in microbial metabolic pathways have recently been confirmed by investigations on the biotransformation of natural compounds.11–13","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":" ","pages":""},"PeriodicalIF":2.5,"publicationDate":"2022-08-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48729155","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Sodium Tungstate Dihydrate (Na2WO4.2H2O): A Mild Oxidizing and Efficient Reagent in Organic Synthesis 二水钨酸钠（Na2WO4.2H2O）：一种温和氧化、高效的有机合成试剂
IF 2.5
SynOpen Pub Date : 2022-08-16 DOI: 10.1055/a-1924-8008
Thaís do Nascimento Pinheiro, E. Barbosa, A. K. Jordão
{"title":"Sodium Tungstate Dihydrate (Na2WO4.2H2O): A Mild Oxidizing and Efficient Reagent in Organic Synthesis","authors":"Thaís do Nascimento Pinheiro, E. Barbosa, A. K. Jordão","doi":"10.1055/a-1924-8008","DOIUrl":"https://doi.org/10.1055/a-1924-8008","url":null,"abstract":"The reagent sodium tungstate dihydrate has some special features which are very important in synthesis. For instance, it is a mild and efficient reagent used in oxidation. Based on reports from recent literature we are proposing this spotlight.","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":" ","pages":""},"PeriodicalIF":2.5,"publicationDate":"2022-08-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49199409","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Recent Applications on Dual-Catalysis for C-C and C-X Cross-Coupling Reactions C-C和C-X交叉偶联反应的双催化研究进展
IF 2.5
SynOpen Pub Date : 2022-07-11 DOI: 10.1055/a-1896-4168
D. Ravi Kishore, Sreenivasulu Chinnabattigalla, Anil Balajirao Dapkekar, G. Satyanarayana
{"title":"Recent Applications on Dual-Catalysis for C-C and C-X Cross-Coupling Reactions","authors":"D. Ravi Kishore, Sreenivasulu Chinnabattigalla, Anil Balajirao Dapkekar, G. Satyanarayana","doi":"10.1055/a-1896-4168","DOIUrl":"https://doi.org/10.1055/a-1896-4168","url":null,"abstract":"Coupling reactions stand amid the most significant reactions in synthetic organic chemistry. Of late, these coupling strategies are being viewed as a versatile synthetic tool for a wide range of organic transformations in many sectors of chemistry, ranging from indispensable synthetic scaffolds and natural products of biological significance to novel organic materials. Further, the usage of dual-catalysis in accomplishing various interesting cross-coupling transformations is an emerging field in synthetic organic chemistry, owing to their high catalytic performance rather than the usage of a single catalyst. In recent years, synthetic organic chemists have given considerable attention to hetero-dual catalysis, wherein these catalytic systems have been employed for the construction of versatile carbon-carbon [C(sp3)–C(sp3), C(sp3)–C(sp2), C(sp2)–C(sp2), etc.] and carbon-heteroatom (C-N, C-O, C-P, C-S, etc.) bonds. Therefore, in this mini-review, we are emphasizing recently developed various cross-coupling reactions catalysed by transition-metal dual-catalysis (i.e., using palladium and copper catalysts, and by omitting the reports on photoredox/metal catalysis).","PeriodicalId":22135,"journal":{"name":"SynOpen","volume":" ","pages":""},"PeriodicalIF":2.5,"publicationDate":"2022-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48818482","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 2
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