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Recent Progress in Accessing Multi-functionalized Caged Hydrocarbons: En Route to Highly-Functionalized Saturated (Bio)isosteres of Benzene Ring 获取多官能化笼状碳氢化合物的最新进展：通向高官能度饱和（生物）苯环异构体之路
Synthesis Pub Date : 2024-07-04 DOI: 10.1055/a-2360-8218
S. Nagasawa, Y. Iwabuchi
{"title":"Recent Progress in Accessing Multi-functionalized Caged Hydrocarbons: En Route to Highly-Functionalized Saturated (Bio)isosteres of Benzene Ring","authors":"S. Nagasawa, Y. Iwabuchi","doi":"10.1055/a-2360-8218","DOIUrl":"https://doi.org/10.1055/a-2360-8218","url":null,"abstract":"Recently, many saturated bioisosteres of benzene ring have been developed, and their application in drug development has been evaluated. Most of these are caged hydrocarbons, which have rigid skeletons and three-dimensional spaces. Recent efforts to synthesize these caged hydrocarbons have enabled access to multi-functionalized congeners that are expected to be (bio)isosteres of multi-functionalized benzenes. This review article summarizes recently reported methods to obtain multi-functionalized (typically more than disubstituted) caged hydrocarbons.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-07-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141680027","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
Selective Synthesis of Deuterated cis- and trans-Isohumulones and trans-Isohumulinones 氘代顺式和反式异胡芦巴内酯及反式异胡芦巴内酯的选择性合成
Synthesis Pub Date : 2024-07-03 DOI: 10.1055/a-2359-8813
Bruce C Hamper, Hunter Campbell, Rensheng Luo, Matthew Murphy, Patrick Gleason, Trevor Smith, Jagan Rajamoni
{"title":"Selective Synthesis of Deuterated cis- and trans-Isohumulones and trans-Isohumulinones","authors":"Bruce C Hamper, Hunter Campbell, Rensheng Luo, Matthew Murphy, Patrick Gleason, Trevor Smith, Jagan Rajamoni","doi":"10.1055/a-2359-8813","DOIUrl":"https://doi.org/10.1055/a-2359-8813","url":null,"abstract":"Deuterated isohumulones can be prepared directly from humulones by an acyloin ring contraction under either magnesium catalyzed basic conditions or photochemical induced reaction in deuterated solvents. Reaction of humulones with biphasic methylene chloride/aqueous NaOD and MgSO4 in D2O gave stereoselective formation of cis-3d- isohumulones (cis-trans ratio of 82:18) as the magnesium salts in 71-83% yield. Greater than 95% incorporation of three deuterons was observed in the C5 position of the pentenone ring and the methylene position of the C4 acyl group. Photochemical isomerization with a 400 nm blue LED source provided stereospecific formation of deuterated trans-isohumulones in 36-82% yield with greater than 95% incorporation of deuterium in the C5 ring position. Oxidation of humulones with cumene hydroperoxide in basic D2O gave isohumulinones with partial 55-73% incorporation of deuterium due to keto-enol isomerization of the methylene substituent of the C4 acyl group. Structural identity of the deuterated products was determined by a combination of negative mode electrospray mass spectrometry (MS-ESI-) and 2D heteronuclear proton-carbon HMQC nmr analysis.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141681246","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
Efficient Flow Synthesis of Glycidyl Ether Using BuSnCl3 as a Mild Lewis Acid 用 BuSnCl3 作为温和的路易斯酸高效流式合成缩水甘油醚
Synthesis Pub Date : 2024-07-03 DOI: 10.1055/a-2359-8893
Takayoshi Kasakado, Masahito Nakamaura, Akihiro Nishizawa, Tetsuya Hosomi, I. Ryu, T. Fukuyama
{"title":"Efficient Flow Synthesis of Glycidyl Ether Using BuSnCl3 as a Mild Lewis Acid","authors":"Takayoshi Kasakado, Masahito Nakamaura, Akihiro Nishizawa, Tetsuya Hosomi, I. Ryu, T. Fukuyama","doi":"10.1055/a-2359-8893","DOIUrl":"https://doi.org/10.1055/a-2359-8893","url":null,"abstract":"A ring-opening protocol of epichlorohydrin (2) with 2-ethylhexanol (1a) was investigated for the synthesis of chlorohydrin 3a. BuSnCl3 proved to be an efficient mild Lewis acid catalyst, yielding 3a with high selectivity. A scalable flow synthesis of 3a was successfully achieved by modifying the flow setup for scaling up. The flow synthesis of glycidyl ether 4a from 3a was also carried out in an efficient manner by using the basic treatment.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141681620","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 Advances in the Synthesis and Applications of Ionic Liquids Derived from Natural Products 天然产品离子液体合成与应用的最新进展
Synthesis Pub Date : 2024-07-03 DOI: 10.1055/s-0043-1775375
Fereshteh Khorasani, Reza Ranjbar-Karimi, Alberto Marra
{"title":"Recent Advances in the Synthesis and Applications of Ionic Liquids Derived from Natural Products","authors":"Fereshteh Khorasani, Reza Ranjbar-Karimi, Alberto Marra","doi":"10.1055/s-0043-1775375","DOIUrl":"https://doi.org/10.1055/s-0043-1775375","url":null,"abstract":"<p>Ionic liquids, nonvolatile salts featuring a melting point below 100 °C, are one of the few alternative solvents for environmentally friendly processes. However, like most molecular solvents, they are usually prepared by means of building blocks derived from fossil oil. Fortunately, an increasing number of ionic liquids are synthesized starting from renewable natural products such as sugars and amino acids. In the present review, we describe the detailed synthesis and applications of the biosourced ionic liquids reported in the literature over the last four years.</p> <p>1 Introduction</p> <p>2 Carbohydrate-Based Ionic Liquids</p> <p>3 Amino Acid Based Ionic Liquids</p> <p>4 Terpene-Based Ionic Liquids</p> <p>5 Miscellaneous Ionic Liquids</p> <p>6 Conclusion</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141550868","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
Silver-Catalyzed Dearomative [3+2] Spiroannulation of Aryl Oxamic Acids with Alkynes 银催化芳基氧肟酸与炔烃的[3+2]螺烷化反应
Synthesis Pub Date : 2024-07-03 DOI: 10.1055/a-2359-8967
Cheng-An Jin, Ren-Xiao Liang, Yi‐Xia Jia
{"title":"Silver-Catalyzed Dearomative [3+2] Spiroannulation of Aryl Oxamic Acids with Alkynes","authors":"Cheng-An Jin, Ren-Xiao Liang, Yi‐Xia Jia","doi":"10.1055/a-2359-8967","DOIUrl":"https://doi.org/10.1055/a-2359-8967","url":null,"abstract":"A silver-catalyzed dearomative decarboxylative [3+2] spiroannulation of aryl oxamic acids with alkynes is described. The reaction provides reliable access to a range of azaspiro[4,5]trienones in moderate yields in aqueous media. In addition, the reaction exhibits a broad substrate scope and good functional group compatibility.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141682675","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 Advances in Ligand-Controlled Regio- or Stereodivergent Transition-Metal-Catalyzed Hydroelementation (H[E]) (E = H, B, Si, Ge) of C–C Unsaturated Systems 配体控制的区域或立体发散过渡金属催化 C-C 不饱和体系氢元素化 (H[E]) （E = H、B、Si、Ge）的最新进展
Synthesis Pub Date : 2024-07-01 DOI: 10.1055/a-2335-8516
Sehoon Park
{"title":"Recent Advances in Ligand-Controlled Regio- or Stereodivergent Transition-Metal-Catalyzed Hydroelementation (H[E]) (E = H, B, Si, Ge) of C–C Unsaturated Systems","authors":"Sehoon Park","doi":"10.1055/a-2335-8516","DOIUrl":"https://doi.org/10.1055/a-2335-8516","url":null,"abstract":"<p>Reductive functionalization of C–C unsaturated systems, including alkenes and alkynes, with a range of hydroelements (H[E]) is one of the most fundamental and highly practical methods for the synthesis of functionalized hydrocarbons. Since the resultant hydrocarbon products have strong applicability as synthetic intermediates, numerous homogeneous organo(metallic) catalysts have been intensively utilized to date for reductive functionalization reactions. In particular, well-defined transition-metal-based catalysts capable of controlling the regio- or stereoselectivity of a product by harnessing the addition of H[E] (E = H, B, Si, Ge) into C<sub>α</sub>–C<sub>β</sub> unsaturated bonds have drawn special attention. In this <i>review</i>, we describe recent examples of transition-metal catalytic systems (M = Fe, Co, Rh, Pd, Ni) for regio- or stereodivergent hydroelementation reactions of (conjugated) alkenes, alkynes, and allenes to give a pair of isomeric products in high selectivities from the same starting compounds simply by variation of the ligand. Mechanistic aspects of the ligand-controlled selectivity divergence are discussed in detail on the basis of experimental observations and/or computational insights.</p> <p>1 Introduction</p> <p>2 Hydroelementation of Alkenes and Alkynes</p> <p>3 Hydroelementation of Conjugated Dienes and Diynes</p> <p>4 Hydroelementation of Allenes</p> <p>5 Summary and Outlook</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141528695","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
1,2-Bis(phenylsulfonyl)ethylene (BPSE): A Potent Radical C2 Synthon Available in the Radical and Electron-Transfer-Based Organic Synthesis 1,2-双（苯磺酰基）乙烯 (BPSE)：可用于基于自由基和电子转移的有机合成的强效自由基 C2 合成物
Synthesis Pub Date : 2024-07-01 DOI: 10.1055/s-0043-1775374
Shuhei Sumino, Ilhyong Ryu, Frédéric Robert, Yannick Landais
{"title":"1,2-Bis(phenylsulfonyl)ethylene (BPSE): A Potent Radical C2 Synthon Available in the Radical and Electron-Transfer-Based Organic Synthesis","authors":"Shuhei Sumino, Ilhyong Ryu, Frédéric Robert, Yannick Landais","doi":"10.1055/s-0043-1775374","DOIUrl":"https://doi.org/10.1055/s-0043-1775374","url":null,"abstract":"<p>In this Short Review, we discuss radical reactions using 1,2-bis(phenylsulfonyl)ethylene (BPSE), which has drawn significant attention as a versatile building block for (phenylsulfonyl)ethenylation. Regardless of its <i>E</i> or <i>Z</i> form, BPSE exhibits reliable reactivity towards the attack of alkyl and aryl radicals in order to function as a reliable radical C2 synthon.</p> <p>1 Introduction</p> <p>2 Use in Radical Chain Reactions</p> <p>3 Use in Reactions Utilizing an Electron-Transfer Process</p> <p>4 Use in Radical-Based C–H Alkenylation</p> <p>5 Conclusion</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141528694","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
An Efficient Promising Direction for the Synthesis of Dispirotripiperazine (6-6-6 DSTP) Core 合成二巯基三哌嗪（6-6-6 DSTP）核心的有效可行方法
Synthesis Pub Date : 2024-06-26 DOI: 10.1055/s-0043-1774930
Mahsa Golmohammadi, Nader Noroozi Pesyan, Ertan Şahin
{"title":"An Efficient Promising Direction for the Synthesis of Dispirotripiperazine (6-6-6 DSTP) Core","authors":"Mahsa Golmohammadi, Nader Noroozi Pesyan, Ertan Şahin","doi":"10.1055/s-0043-1774930","DOIUrl":"https://doi.org/10.1055/s-0043-1774930","url":null,"abstract":"<p>A new and facile route for the one-pot synthesis of 3,12-dicyano-3,6,9,12-tetraazadispiro[5.2.5<sup>9</sup>.2<sup>6</sup>]hexadecane-6,9-diium dibromide as a dispirotripiperazine source was introduced by the simple reaction of 1,4-diazabicyclo[2.2.2]octane (DABCO) with cyanogen bromide (BrCN) under mild condition at room temperature. The hydrolysis of dicyanamide moieties in the prepared dispiro compound gave 3,12-diaza-6,9-diazoniadispiro[5.2.5.2]hexadecane dibromide with the dispirotripiperazine (6-6-6) core. The molecular structure of the new compound was characterized by FT-IR, <sup>1</sup>H, <sup>13</sup>C, HSQC NMR spectroscopy, mass and CHN analysis, and X-ray crystallography technique.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-06-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141501752","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
Benzothiazole-Directed Enantioselective Borylation of Secondary Benzylic C–H Bonds Using Iridium Catalysis 利用铱催化实现苯并噻唑引导的仲苄基 C-H 键对映选择性硼酰化反应
Synthesis Pub Date : 2024-06-24 DOI: 10.1055/a-2335-8677
Liang-Jun Xie, Lili Chen, Senmiao Xu
{"title":"Benzothiazole-Directed Enantioselective Borylation of Secondary Benzylic C–H Bonds Using Iridium Catalysis","authors":"Liang-Jun Xie, Lili Chen, Senmiao Xu","doi":"10.1055/a-2335-8677","DOIUrl":"https://doi.org/10.1055/a-2335-8677","url":null,"abstract":"<p>Reported here is the iridium-catalyzed regio- and enantio­selective secondary benzylic C–H borylation using benzothiazole as the directing group. Various monosubstituted 2-arylalkylbenzo[<i>d</i>]thiazole were well-tolerated, affording the corresponding products in moderate to good yields with good enantioselectivity. The C–B bond in one boryl­ated product could undergo stereospecific transformations to form a series of C–C and C–heteroatom bonds.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-06-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141528654","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
A Practical Electrochemical Approach for Synthesizing Selenyl-Dihydrobenzofurans and Chromane with a Tetrasubstituted Carbon Center 合成硒基二氢苯并呋喃和以四取代碳为中心的铬烷的实用电化学方法
Synthesis Pub Date : 2024-06-24 DOI: 10.1055/s-0043-1775373
Qisheng Chen, Kai Xiang, Yiyi Chen, Xianqiang Kong, Xiaohui Chen, Zhong-Yan Cao
{"title":"A Practical Electrochemical Approach for Synthesizing Selenyl-Dihydrobenzofurans and Chromane with a Tetrasubstituted Carbon Center","authors":"Qisheng Chen, Kai Xiang, Yiyi Chen, Xianqiang Kong, Xiaohui Chen, Zhong-Yan Cao","doi":"10.1055/s-0043-1775373","DOIUrl":"https://doi.org/10.1055/s-0043-1775373","url":null,"abstract":"<p>A straightforward and efficient electrochemical method for the anodic oxidative selenenylation of 2-(2-arylallyl)phenols and a 2-(3-arylbut-3-en-1-yl)phenol with diselenides under ambient air conditions has been outlined. This method allows for the synthesis of selenyl-dihydrobenzofurans and a chromane featuring a sterically hindered tetrasubstituted carbon center, demonstrated through 25 examples with yields reaching up to 98%. Initial mechanistic investigations suggest the likely participation of pivotal seleniranium cation species in regulating the reactivity.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2024-06-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141528776","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
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