{"title":"Synthetic Development of Key Intermediates and Active Pharmaceutical Ingredients (APIs)","authors":"Joydev K. Laha, Jianrong Steve Zhou","doi":"10.1055/s-0040-1720106","DOIUrl":"https://doi.org/10.1055/s-0040-1720106","url":null,"abstract":"","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":"45 14","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140488333","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}
H. V. Rasika Dias, C. J. Lovely, Panduka B. Koswatta, R. Sivappa
{"title":"Erratum - Total Synthesis of the Leucetta-Derived Alkaloid Calcaridine A","authors":"H. V. Rasika Dias, C. J. Lovely, Panduka B. Koswatta, R. Sivappa","doi":"10.1055/s-0040-1720105","DOIUrl":"https://doi.org/10.1055/s-0040-1720105","url":null,"abstract":"","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":"7 2","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140489821","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}
Cong So Tran, Moonsang Yoon, Long Duc Le, Seoyeong Kim, Huiae Kim, Jisu Kim, Long Huu Nguyen, Minseob Koh, Hwayoung Yun
Concise and strategically unique asymmetric formal syntheses of epi-mutisianthol and epi-jungianol are presented. A novel disconnection approach is introduced to complement previous intramolecular cyclopentannulation strategies. Noteworthy features include: (a) the control of the stereogenic benzylic carbon center through 1,3-chirality transfer from chiral indenols via the Johnson-Claisen rearrangement, which yields advanced indene-containing γ,δ-unsaturated esters, and (b) the diastereoselective construction of the cis-1,3-dialkylindane backbone via catalytic hydrogenation of the resulting indene. This approach presents a remarkable method for synthesizing structurally intriguing indane motifs.
{"title":"Rapid Access to cis-1,3-Dialkylindanes: Asymmetric Formal Syntheses of epi-Mutisianthol and epi-Jungianol","authors":"Cong So Tran, Moonsang Yoon, Long Duc Le, Seoyeong Kim, Huiae Kim, Jisu Kim, Long Huu Nguyen, Minseob Koh, Hwayoung Yun","doi":"10.1055/a-2249-2326","DOIUrl":"https://doi.org/10.1055/a-2249-2326","url":null,"abstract":"Concise and strategically unique asymmetric formal syntheses of epi-mutisianthol and epi-jungianol are presented. A novel disconnection approach is introduced to complement previous intramolecular cyclopentannulation strategies. Noteworthy features include: (a) the control of the stereogenic benzylic carbon center through 1,3-chirality transfer from chiral indenols via the Johnson-Claisen rearrangement, which yields advanced indene-containing γ,δ-unsaturated esters, and (b) the diastereoselective construction of the cis-1,3-dialkylindane backbone via catalytic hydrogenation of the resulting indene. This approach presents a remarkable method for synthesizing structurally intriguing indane motifs.","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":"80 16","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139526343","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}
Here, we wish to describe our detailed efforts of the total synthesis of three calyciphylline A-type alkaloids, namely (+)-daphlongamine E, (+)-calyciphylline R, and (−)-10-deoxydaphnipaxianine A. Important steps in our approach include a Pt-catalyzed nitrile hydration, a Babler–Dauben rearrangement, a novel selective amide reduction tactic and, an oxidative Nazarov cyclization via an unfunctionalized tertiary divinyl carbinol (TDC).
在此，我们希望详细描述一下我们对三种萼片紫碱 A 型生物碱（即 (+)-daphlongamine E、(+)-萼片紫碱 R 和 (-)-10-deoxydaphnipaxianine A）进行全合成的过程。我们研究方法的重要步骤包括铂催化的腈水合反应、巴伯勒-道本重排反应、新型选择性酰胺还原反应以及通过未官能化的叔二乙烯基卡宾醇（TDC）进行氧化纳扎罗夫环化反应。
{"title":"Total Synthesis of Daphniphyllum Alkaloids: (+)-Daphlongamine E, (+)-Calyciphylline R, and (−)-10-Deoxydaphnipaxianine A","authors":"Yan Zhang, Yuye Chen, Jing Xu","doi":"10.1055/a-2244-1600","DOIUrl":"https://doi.org/10.1055/a-2244-1600","url":null,"abstract":"Here, we wish to describe our detailed efforts of the total synthesis of three calyciphylline A-type alkaloids, namely (+)-daphlongamine E, (+)-calyciphylline R, and (−)-10-deoxydaphnipaxianine A. Important steps in our approach include a Pt-catalyzed nitrile hydration, a Babler–Dauben rearrangement, a novel selective amide reduction tactic and, an oxidative Nazarov cyclization via an unfunctionalized tertiary divinyl carbinol (TDC).","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":"45 19","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139533517","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}
Synthesis of thiazole-fused derivatives of tricyclic quinazolinones hitherto undescribed was successfully achieved by replacing anthranilic acid or its derivatives by isomeric polyfunctionalized benzothiazole analogues of anthranilic methyl esters. Some of the new heterocyclic systems are inspired by natural alkaloids such as mackinazolinone, deoxyvasicinone and isaindigotone, showing interesting biological properties. The microwave-assisted method developed is a variant of the Niementowski reaction and was also applied to the synthesis of ring-extended rutaecarpine derivatives.
{"title":"SYNTHESIS OF THIAZOLE-FUSED TRICYCLIC QUINAZOLINONE ALKALOIDS AND THEIR DERIVATIVES","authors":"Nathan Broudic, Corentin Layec, Corinne Fruit, Thierry Besson","doi":"10.1055/a-2243-4727","DOIUrl":"https://doi.org/10.1055/a-2243-4727","url":null,"abstract":"Synthesis of thiazole-fused derivatives of tricyclic quinazolinones hitherto undescribed was successfully achieved by replacing anthranilic acid or its derivatives by isomeric polyfunctionalized benzothiazole analogues of anthranilic methyl esters. Some of the new heterocyclic systems are inspired by natural alkaloids such as mackinazolinone, deoxyvasicinone and isaindigotone, showing interesting biological properties. The microwave-assisted method developed is a variant of the Niementowski reaction and was also applied to the synthesis of ring-extended rutaecarpine derivatives.","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":"36 20","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139534101","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}
An efficient K2CO3-mediated intramolecular oxa-Michael cyclization of β,β-diarylated-α,β-unsaturated ketoximes has been described. This methodology features arene-rich 2-isoxazoline derivatives bearing one quaternary center in excellent yields with operationally simple experimental procedure. The deuterium scrambling experiments were carried out to shed light on the reaction pathway. To further demonstrate the synthetic utility of the method, a large-scale synthesis and Ullmann-type C-N bond formation reaction between pyrazole and dibrominated-isoxazoline have been performed.
{"title":"K2CO3-Mediated Intramolecular Oxa-Michael Cyclization of α,β–Unsaturated Ketoximes: Synthesis of Densely Arene-Substituted 2-Isoxazolines Bearing One Quaternary Center","authors":"M. Bhanuchandra, R. Jat, Raveendrababu Kothapalli","doi":"10.1055/a-2242-6435","DOIUrl":"https://doi.org/10.1055/a-2242-6435","url":null,"abstract":"An efficient K2CO3-mediated intramolecular oxa-Michael cyclization of β,β-diarylated-α,β-unsaturated ketoximes has been described. This methodology features arene-rich 2-isoxazoline derivatives bearing one quaternary center in excellent yields with operationally simple experimental procedure. The deuterium scrambling experiments were carried out to shed light on the reaction pathway. To further demonstrate the synthetic utility of the method, a large-scale synthesis and Ullmann-type C-N bond formation reaction between pyrazole and dibrominated-isoxazoline have been performed.","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":"67 26","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139534746","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}
Dewal S. Deshmukh, Nikunjkumar Vagadiya, Samadhan Jagatap, Pravin Malasane
This review deals with the developing field of C–H activation reactions and particularly focuses on green catalysis through the use of environmentally friendly solvents. It evaluates the effects of these solvents on reactions outcomes, environmental aspects and general efficacy pointing out their advantages lead to greater selectivity, lower level of toxicity and enhanced reaction rates. Water and biobased alternatives such as Polyethylene glycols, Ethanol, Gamma-valerolactone, Methanol, p-cymene or 2-methyltetrahydrofurane, Glycerol or Di ethyl carbonate represent representative examples of such solvents. Its scope encompasses the study of different methodologies, catalysts, and reaction conditions that help to develop C–H activation reactions with green solvents.
{"title":"Revolutionizing C–H Activation Reactions: Harnessing Green Solvents for Sustainable Catalysis","authors":"Dewal S. Deshmukh, Nikunjkumar Vagadiya, Samadhan Jagatap, Pravin Malasane","doi":"10.1055/a-2241-6858","DOIUrl":"https://doi.org/10.1055/a-2241-6858","url":null,"abstract":"This review deals with the developing field of C–H activation reactions and particularly focuses on green catalysis through the use of environmentally friendly solvents. It evaluates the effects of these solvents on reactions outcomes, environmental aspects and general efficacy pointing out their advantages lead to greater selectivity, lower level of toxicity and enhanced reaction rates. Water and biobased alternatives such as Polyethylene glycols, Ethanol, Gamma-valerolactone, Methanol, p-cymene or 2-methyltetrahydrofurane, Glycerol or Di ethyl carbonate represent representative examples of such solvents. Its scope encompasses the study of different methodologies, catalysts, and reaction conditions that help to develop C–H activation reactions with green solvents.","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":"61 21","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139534847","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}
A simple and efficient method for the synthesis of 1,4-dihydropyridines from amines, N,N-dimethyl enaminone and N,N-dimethylaminoethanol in a four-component [2+1+2+1] annulation catalyzed by FeCl3 has been established, where N,N-dimethylaminoethanol was applied as a methine source. The procedure was executed smoothly, resulting in the synthesis of a wide range of 1,4-dihydropyridines with moderate to good yields. Additionally, these fluorophores exhibited good photophysical characteristics.
{"title":"Iron-Catalyzed [2+1+2+1] Annulation of Amines and N,N-Dimethyl Enaminones using N,N-dimethylaminoethanol as One Carbon Synthon for the Synthesis of 1,4-Dihydropyridines.","authors":"Wanqian Ma, Qiulin Kuang, Suzhen Li, Mengyi Guo, Yibo Song, Luoteng Cheng, JianYong Yuan","doi":"10.1055/a-2241-2196","DOIUrl":"https://doi.org/10.1055/a-2241-2196","url":null,"abstract":"A simple and efficient method for the synthesis of 1,4-dihydropyridines from amines, N,N-dimethyl enaminone and N,N-dimethylaminoethanol in a four-component [2+1+2+1] annulation catalyzed by FeCl3 has been established, where N,N-dimethylaminoethanol was applied as a methine source. The procedure was executed smoothly, resulting in the synthesis of a wide range of 1,4-dihydropyridines with moderate to good yields. Additionally, these fluorophores exhibited good photophysical characteristics.","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":"13 5","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139444098","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}
The atroposelective transformation of alkynes is an efficient protocol for the assembly of axially chiral compounds. Benefit from the rapid development of chiral organocatalysts, the organocatalytic atroposelective reactions of alkynes have been extensively studied during the past decades. An array of chiral catalysts, including chiral Brønsted acid catalysts, secondary amine catalysts, N-heterocyclic carbene (NHC) catalysts, thiourea catalysts and N-squaramide catalysts, were employed into the enantioselective reactions of different alkynes. This review summarizes the recent advances in organocatalytic atroposelective reactions of alkynes according to the types of alkyne substrates. The reaction mechanisms, mode of enantiocontrol, product diversity and applications are highlighted in this review.
{"title":"Organocatalytic Atroposelective Reactions of Alkynes","authors":"Zhi-Xin Zhang, Tian-Qi Hu, Long-Wu Ye, Bo Zhou","doi":"10.1055/a-2241-3571","DOIUrl":"https://doi.org/10.1055/a-2241-3571","url":null,"abstract":"The atroposelective transformation of alkynes is an efficient protocol for the assembly of axially chiral compounds. Benefit from the rapid development of chiral organocatalysts, the organocatalytic atroposelective reactions of alkynes have been extensively studied during the past decades. An array of chiral catalysts, including chiral Brønsted acid catalysts, secondary amine catalysts, N-heterocyclic carbene (NHC) catalysts, thiourea catalysts and N-squaramide catalysts, were employed into the enantioselective reactions of different alkynes. This review summarizes the recent advances in organocatalytic atroposelective reactions of alkynes according to the types of alkyne substrates. The reaction mechanisms, mode of enantiocontrol, product diversity and applications are highlighted in this review.","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":"22 19","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139443219","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}
The copper-catalyzed enantioselective radical esterification of propargylic C−H bonds with tert-butyl peroxybenzoate (TBPB) as oxidizing agent and oxygenated nucleophile has been reported. This variant of the Kharasch-Sosnovsky oxidation allows for the asymmetric esterification of open-chain carbon radicals without excessive amounts of alkyne substrates under mild reaction conditions, achieving a one-step conversion from simple alkynes to chiral propargylic esters.
{"title":"Copper-Catalyzed Enantioselective Radical Esterification of Propargylic C−H Bonds","authors":"Jiajia Xi, Xiaotao Zhu, H. Bao","doi":"10.1055/a-2240-5349","DOIUrl":"https://doi.org/10.1055/a-2240-5349","url":null,"abstract":"The copper-catalyzed enantioselective radical esterification of propargylic C−H bonds with tert-butyl peroxybenzoate (TBPB) as oxidizing agent and oxygenated nucleophile has been reported. This variant of the Kharasch-Sosnovsky oxidation allows for the asymmetric esterification of open-chain carbon radicals without excessive amounts of alkyne substrates under mild reaction conditions, achieving a one-step conversion from simple alkynes to chiral propargylic esters.","PeriodicalId":510101,"journal":{"name":"Synthesis","volume":"24 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139445427","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}
京公网安备 11010802042870号
京ICP备2023020795号-1
扫码关注我们
求助内容：
应助结果提醒方式：