Article
Chemistry, Multidisciplinary
Yusuke Imamura, Kyohei Takaoka, Yuma Komori, Masanori Nagatomo, Masayuki Inoue
Summary: This study presents a 34-step synthesis of Taxol, involving inter- and intramolecular radical reactions to connect the A- and C-ring fragments and cyclize the B-ring. The A- and C-ring functional groups were then efficiently modified using newly developed selective reactions. The construction of the D-ring and its conjugation with the beta-amino acid led to the successful synthesis of Taxol. This synthesis provides useful insights for the design of multistep syntheses of diverse bioactive natural products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Nicole Hauser, Michael A. Imhof, Sarah S. Eichenberger, Tomas Kundig, Erick M. Carreira
Summary: The first total syntheses of the indole diterpenoids (+)-shearinine G and D were achieved through late-stage coupling, diastereoselective intramolecular cyclopropanation, Sharpless dihydroxylation/Achmatowicz reaction, and Prins cyclization. Tuning of the substituents on the parent arylcarboxaldehyde led to divergent products, further transformed into shearinines G and D, with unexpected stereochemical outcomes in the Riley-type oxidation of a bicyclic enone.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Guanggen Liu, Zhijiang Zhang, Shaomin Fu, Bo Liu
Summary: The first asymmetric total synthesis of rumphellclovane E was accomplished in eight steps from commercially available (R)-carvone. Key elements of the synthesis included Rh-catalyzed cyclopropanation, iron-catalyzed intramolecular reductive aldol reaction, and SmI2-mediated chemo- and diastereoselective reduction of the cyclopentanone.
Article
Chemistry, Multidisciplinary
Debasish Ghorai, Aleria Garcia-Roca, Balazs L. Toth, Jordi Benet-Buchholz, Arjan W. Kleij
Summary: This article reports the regio- and enantioselective synthesis of chiral 1,5-dienes featuring quaternary stereocenters via nickel-promoted reductive homoallylic coupling. The developed methodology can selectively form unusual branched regioisomers and improve the enantiomeric and chemo-selectivity of the products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Enno Aeissen, Aaron R. von Seggern, Marc Schmidtmann, Jens Christoffers
Summary: In this study, cyclopenta-, benzo-, and cyclohepta[b]-annulated azepane scaffolds were efficiently synthesized from optically active cyclic alpha-allyl-beta-oxoesters. The synthesis involves two steps: ruthenium-catalyzed olefin cross metathesis with acrylonitrile, followed by palladium-catalyzed dihydrogenation consisting of hydrogenation, reductive amination, and cyclization reactions. The annulated azepanes with relative trans-configuration were obtained selectively. The amino and ester functionalities further provide opportunities for diversification of the scaffolds. The enantiopurity and relative trans-configurations of the products were confirmed by chiral phase GLC analysis and X-ray crystallography, respectively.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Ryota Ogura, Kazuto Satoh, Wataru Kiuchi, Kosuke Kato, Kazutada Ikeuchi, Takahiro Suzuki, Keiji Tanino
Summary: A two-step synthesis of geminal divinyl compounds from ketones was developed. An allyl titanium reagent reacted with a ketone to form a tertiary alcohol, which was then subjected to a rearrangement reaction mediated by a Bronsted acid to generate a geminal divinyl compound. Introduction of another alkene moiety followed by ring closing metathesis resulted in a bicyclic compound possessing a vinyl group at the bridgehead position.
Article
Chemistry, Organic
Jiang Lou, Wenjia Han, Zhuqing Liu, Jiaqi Xiao
Summary: The Rh(III)-catalyzed enone carbonyl directed annulative coupling of alpha-aroyl ketene dithioacetals and diazo compounds enables the synthesis of highly functionalized indanone derivatives with a quaternary carbon stereocenter at the beta-position. This protocol demonstrates high efficiency, broad substrate scope, and high compatibility with functional groups.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Jeremy Nugent, Alistair J. Sterling, Nils Frank, James J. Mousseau, Edward A. Anderson
Summary: Bicyclo[1.1.1]pentanes (BCPs) are synthesized efficiently using organophotoredox and hydrogen atom transfer catalysis, allowing for the preparation of alpha-quaternary BCPs. The products can be further transformed into a variety of useful derivatives, including enantioenriched BCPs.
Article
Chemistry, Organic
Davit Hayrapetyan, Valeriya Stepanova
Summary: In this study, spirocyclic pyrrolidones and piperidones were synthesized via [3+2]- and [3+3]-aza-annulation reactions starting from readily available alpha-ketolactones and alpha-ketolactams. The annulation reactions proceeded with good yields and excellent diastereoselectivity, creating one C-C and two C-N bonds, as well as three new stereocenters in a fast and efficient manner.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Weiping Zhou, Arnaud Voituriez
Summary: A cationic gold(I)-catalyzed asymmetric [3,3]-sigmatropic rearrangement of sulfonium leads to the formation of cyclopentenones with a C4-quaternary stereocenter after cyclization. This methodology was successfully applied to the efficient total synthesis of five natural sesquiterpenoids, demonstrating moderate to good yields and excellent enantiomeric excesses in 26 examples.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Swamy Peraka, Badaraita Gorachand, Akram Hussain, Revoju Sravanthi, Dhevalapally B. Ramachary
Summary: Structurally complex cedrane scaffolds were synthesized in high yields and selectivities using a sequential one-pot method. This green synthesis approach demonstrates the unique combination of coupling and annulation routes, with the highlight on organocatalytic ring isomerization.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
A. Yu Sidorenko, Yu M. Kurban, A. Kravtsova, I. Il'ina, N. S. Li-Zhulanov, D. Korchagina, J. E. Sanchez-Velandia, A. Aho, K. P. Volcho, N. F. Salakhutdinov, D. Yu Murzin, V. E. Agabekov
Summary: The Prins/Friedel-Crafts cascade reactions of terpenoid trans-4-hydroxymethyl-2-carene with aromatic aldehydes were systematically studied for the first time on acidic mesoporous clays. The study found that catalyst acidity and drying temperature play key roles in influencing both reaction rate and selectivity. Montmorillonites were shown to be effective replacements for homogeneous catalysts in these cascade reactions.
APPLIED CATALYSIS A-GENERAL
(2022)
Article
Chemistry, Multidisciplinary
Zhuang Chen, Kuan Zhao, Yanxing Jia
Summary: This study presents a bioinspired total synthesis of (+)-euphorikanin A, which features a fascinating and intricate tetracyclic skeleton with a bridged [3.2.1]-gamma-lactone moiety. Key transformations involve stereoselective alkylation and aldol condensation to introduce the main stereocenters, an intramolecular nucleophile-catalyzed aldol lactonization of carboxylic acid-ketone to form the five-membered ring, a McMurry coupling to construct the seven-membered ring, and a biomimetic benzilic acid type rearrangement to generate the bridged [3.2.1]-gamma-lactone moiety.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Xi Wang, Fujie Liu, Tao Xu
Summary: This study describes a visible light induced catalytic [2 + 2] cycloaddition approach that selectively constructs up to four contiguous quaternary carbon stereocenters in a pentacyclic fused ring system from readily accessible dienamides with pendent heteroaryls. Mechanistic studies revealed an uncommon beta-C radical initiated 7-endo cyclization from the biradical intermediate.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Physical
Jialin Qi, Tingting Song, Zhenning Yang, Shuzhe Sun, Chen-Ho Tung, Zhenghu Xu
Summary: A stereodivergent synthesis of chiral beta-lactams with contiguous tertiary/quaternary/tertiary stereocenters has been achieved. The strategy involves a Cu/Ir-catalyzed three-component interrupted Kinugasa allylic alkylation reaction, which provides access to four of the eight possible stereoisomers with high yields and >99% ee. The key features are the asymmetric simultaneous dual metal-catalyzed cascade reactions with stereoselective coupling of highly transient organometallic intermediates.
Article
Chemistry, Multidisciplinary
Pawel Czerwinski, Edyta Molga, Luigi Cavallo, Albert Poater, Michal Michalak
CHEMISTRY-A EUROPEAN JOURNAL
(2016)
Article
Chemistry, Organic
Karol Wolosewicz, Michal Michalak, Jakub Adamek, Bartlomiej Furman
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Karol Michalak, Maja Morawiak, Jerzy Wicha
Article
Polymer Science
P. Horeglad, M. Cybularczyk, A. Litwinska, A. M. Dabrowska, M. Dranka, G. Z. Zukowska, M. Urbanczyk, M. Michalak
Article
Chemistry, Organic
Karol Michalak, Jerzy Wicha, Jacek Wojcik
Article
Chemistry, Organic
Pawel Czerwinski, Michal Michalak
JOURNAL OF ORGANIC CHEMISTRY
(2017)
Review
Biochemistry & Molecular Biology
Michal Michalak, Karol Michalak, Jerzy Wicha
NATURAL PRODUCT REPORTS
(2017)
Article
Chemistry, Physical
I. Misztalewska-Turkowicz, K. H. Markiewicz, M. Michalak, A. Z. Wilczewska
JOURNAL OF CATALYSIS
(2018)
Review
Chemistry, Organic
Pawel J. Czerwinski, Michal Michalak
SYNTHESIS-STUTTGART
(2019)
Review
Chemistry, Physical
Michal Michalak, Wioletta Kosnik
Article
Chemistry, Organic
Michal Michalak, Bartosz Bisek, Michal Nowacki, Marcin Gorecki
Summary: A novel method for synthesizing V-shaped molecular epoxydibenzo[b,f][1,5]diazocines has been reported, utilizing a rigid scaffold that allows for enantiomer separation and high thermal stability. The inertness of the molecular architecture was demonstrated through various typical reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Physical
Paulina Baczewska, Katarzyna Sniady, Wioletta Kosnik, Michal Michalak
Summary: N-Heterocyclic carbene (NHC) ligands have become a privileged structural motif in modern homogeneous and heterogeneous catalysis, especially in the area of carbon-carbon bond formation. NHC ligands derived from acenaphthylene with a pi-extended system show superior sigma-donor capabilities, enhancing catalytic activity and stability in transition metal complexes.
Article
Chemistry, Organic
Magdalena Dolna, Michal Nowacki, Oksana Danylyuk, Artur Brotons-Rufes, Albert Poater, Michal Michalak
Summary: This study developed a direct catalytic alkynylation/dehydrative cyclization method on water for the synthesis of a broad range of fluorinated 1,8-naphthyridines from 2-amino-3-trifluoroacetyl-pyridines and terminal alkynes. A unique N-heterocyclic carbene (NHC) ligand system was successfully utilized for copper- or silver-mediated cyclization. Computational analysis of the reaction pathway supported the explanation of different experimental conversions and yields for copper and silver catalysts.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Organic
Wojciech Depa, Bartosz Bisek, Marcin Gorecki, Michal Michalak
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
