Article
Chemistry, Multidisciplinary
Xin Gao, Dirk Menche
Summary: Two novel tandem sequences for stereoselective synthesis of elaborate hydropyranones are described. The first approach involves aldol-lactonization of a chiral enolate with an unprotected aldehyde, while the second approach entails a dienolate ketone addition along with cyclization and substrate controlled reduction. Both methods exhibit high efficiency and stereoselectivity, providing expedient access to the pyranone subunit of the complex polyketide tuscolid. These methods are crucial for developing the first total synthesis of tuscolid, a structurally unique macrolide, and for evaluating the tuscolid-tuscoron rearrangement.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Sovan Biswas, Ben F. Van Steijvoort, Marjo Waeterschoot, Narendraprasad Reddy Bheemireddy, Gwilherm Evano, Bert U. W. Maes
Summary: Bridged nitrogen bicyclic skeletons have been accessed via unprecedented site- and diastereoselective orthogonal tandem catalysis from readily accessible reactants in a step economic manner. The protocol allows for the preparation of substituted analogues with ease, and the use of a Cu catalyst in the Ullmann-Goldberg reaction helps avoid interference from off-cycle Pd catalyst scavenging.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Yoarhy A. Amador-Sanchez, Pedro Lopez-Mendoza, Marco Mijangos, Luis D. Miranda
Summary: This synthesis protocol efficiently produces poly-functionalized compounds through a series of reactions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Shuailong Li, Zhuangxing Li, Mingzheng Li, Lin He, Xumu Zhang, Hui Lv
Summary: In this study, an efficient method for enantioselective construction of bridged [2,2,1] bicyclic lactones bearing a quaternary stereocenter via Rh-catalyzed asymmetric hydroformylation/intramolecular cyclization/pyridinium chlorochromate oxidation was reported, resulting in high yields and excellent enantiomeric excess. The methodology offers a convenient approach for the synthesis of important scaffolds widely occurring in both pharmaceutics and bioactive compounds.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Hikaru Yanai, Teru Kawazoe, Nobuyuki Ishii, Bernhard Witulski, Takashi Matsumoto
Summary: In this study, 4-aryl-1,3-dihydroxy-2-naphthoates with the less accessible 1,2,3,4-tetrasubstituted naphthalene scaffold were selectively synthesized from brominated lactol silyl ethers through the 1,2-aryl-migrative ring rearrangement reaction, showing photoluminescence emission in both solid state and solutions.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Ameya S. Burde, Shuklendu D. Karyakarte, Eric D. Sylvester, Sherry R. Chemler
Summary: Bridged bicyclic ketals with a range of bioactivities can be synthesized from acyclic 1,1-disubstituted alkene diols using catalytic enantioselective synthesis. This reaction combines asymmetric catalysis with a distal radical migration, with alkynes and arenes undergoing group transfer.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Emma Naulin, Marine Lombard, Vincent Gandon, Pascal Retailleau, Elsa Van Elslande, Luc Neuville, Geraldine Masson
Summary: This study reports a method for selectively controlling the regioselectivity of conjugated trienes and synthesizing chiral cis-3,6-dihydro-2H-1,2-oxazines. Modular access to three different regioisomers is achieved, and the utility of each regioisomeric cycloadduct is highlighted.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Daniel S. Brandes, Ana Sirvent, Brandon Q. Mercado, Jonathan A. Ellman
Summary: The three-component method described enables the preparation of diverse synthetic compounds with different structures, and asymmetric synthesis of products can be achieved using a chiral Cp-derived Rh-III catalyst.
Article
Chemistry, Organic
Roman S. Malykhin, Ivan S. Golovanov, Yulia Nelyubina, Sema L. Ioffe, Alexey Yu Sukhorukov
Summary: The reaction between six-membered cyclic nitronates and disubstituted ketenes can produce saturated oxazolo[3,2-b][1,2]-oxazines with up to four contiguous stereogenic centers. The process involves a tandem of [3+2]-cycloaddition and [1,3]-rearrangement, leading to the formation of precursors for other fused oxazine derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Harbansh Singla, Sandeep Kumar, Jyotirmoy Maity, Ashok K. Prasad
Summary: A greener chemo-enzymatic methodology has been developed for synthesizing conformationally restricted diastereomeric AZT analogues. The primary hydroxyl group of 3'-azido-3'-deoxy-beta-D-glucofuranosyl pyrimidines was acetylated using Novozyme (R) 435, and then converted to the desired bicyclic AZT analogue.
CARBOHYDRATE RESEARCH
(2023)
Article
Chemistry, Organic
Vitaly V. Shorokhov, Sergey S. Zhokhov, Victor B. Rybakov, Maksim A. Boichenko, Ivan A. Andreev, Nina K. Ratmanova, Igor V. Trushkov, Olga A. Ivanova
Summary: A Lewis acid-promoted domino ring-opening cyclization of readily available donor-acceptor cyclopropanes with a preinstalled electrophilic center, embedded in a donor group, to functionalized 1,2-dihydronaphthalenes is reported. The obtained compounds are transformed to pharmacologically attractive bridged tricyclic esters in a diastereospecific manner.
Article
Chemistry, Organic
Palani Manikandan, Rudrasenan Agneswaran, Vinayagam Pavunkumar, Arasambattu K. Mohanakrishnan
Summary: Heteroarylmethylenephosphorus ylides can react with alkynediones and alkynediesters to yield various organic compounds.
Article
Chemistry, Multidisciplinary
Xiaohu Li, You Huang
Summary: A phosphine-catalyzed cascade (2+3)/(2+4) cyclization reaction has been developed for the synthesis of chromeno[4,3-b]pyrrole derivatives. This method provides good yield, excellent chemoselectivity and diastereoselectivity under mild conditions, resulting in compounds containing three contiguous stereogenic centers.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Mohammad Rezaei-Gohar, Kamran Amiri, Kimia Aghaie, Behrouz Nayebzadeh, Alireza Ariafard, Farshad Shiri, Frank Rominger, Dmitry Dar'in, Mikhail Krasavin, Saeed Balalaie
Summary: An efficient procedure for accessing a wide variety of interconnected imidazo[1,2-a]pyridine and benzimidazole skeletons through the C-N bond using a new type of Buchwald-Hartwig reaction is described. Furthermore, changing the equivalent ratio of starting materials allows for the synthesis of bis(imidazo[1,2-a]pyridin-3-yl)aryl-1,2-diamine scaffolds. The protocol offers several advantages, including the formation of four new bonds (C=C, C-N), a transition-metal-free reaction, a broad substrate scope, high yields, and mild reaction conditions. The reaction mechanism is confirmed by DFT calculations.
Article
Chemistry, Multidisciplinary
Yuhang Chen, Dingcheng Zhang, Mingze Sun, Zhenhua Ding
Summary: The divergent synthesis of isoxazoles and 6H-1,2-oxazines was achieved using a hypervalent fluoroiodane reagent from beta,gamma-unsaturated oximes. The size of the ring formed in the reaction was controlled by the substituents of the substrates and the reaction conditions. The reaction proceeded under mild conditions and provided moderate to good yields.
NEW JOURNAL OF CHEMISTRY
(2022)
