Synthesis of (–)-Gukulenin B DOI

Synfacts, Journal Year: 2022, Volume and Issue: 18(06), P. 0582 - 0582

Published: May 17, 2022

Key words (–)-gukulenin B - tropolonoid marine natural product tropolone functionalization aldol reaction Shapiro retro-Michael

Language: Английский

Metal-catalysed C–H bond activation and borylation DOI

Ranjana Bisht,

Chabush Haldar, Mirja Md Mahamudul Hassan

et al.

Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(12), P. 5042 - 5100

Published: Jan. 1, 2022

Transition metal-catalysed direct borylation of hydrocarbons via C–H bond activation has received a remarkable level attention as popular reaction in the synthesis organoboron compounds owing to their synthetic versatility.

Language: Английский

Citations

195
Marine natural products DOI Creative Commons
Anthony R. Carroll, Brent R. Copp, Tanja Grkovic

et al.

Natural Product Reports, Journal Year: 2024, Volume and Issue: 41(2), P. 162 - 207

Published: Jan. 1, 2024

A comprehensive review of 1411 new MNPs and their structural diversity analysis including the cyanobacterial metabolite lezoside.

Language: Английский

Citations

75
C–H borylation: a tool for molecular diversification DOI
Saikat Guria, Mirja Md Mahamudul Hassan, Buddhadeb Chattopadhyay

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(3), P. 929 - 953

Published: Dec. 19, 2023

Iridium-catalyzed C–H activation and borylation has become as a powerful synthetic tool in the past few decades because of widespread applicability versatility organoboron compounds.

Language: Английский

Citations

21
Electrochemical Nickel-Catalyzed C(sp2)-H Functionalization of Tropones with Aldehydes DOI Creative Commons
Andrea Brunetti, Sofia Kiriakidi,

Mauro Garbini

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 3184 - 3190

Published: Feb. 6, 2025

A direct electroreductive functionalization of tropones employing aldehydes as alkylating agents is reported. This C(sp2)-H process leverages the mediation electroactive nickel complexes, enabling a wide range both native and substituted (44 examples) to be alkylated selectively at α-position in high yields (up 90%). Combined electrochemical, spectroelectrochemical, computational analyses disclosed whole mechanistic pathway revealed key role played by reduced Ni complexes activating tropone core toward condensation with aldehydes.

Language: Английский

Citations

1
Carbocycloaddition strategies for troponoid synthesis DOI Creative Commons
Ryan P. Murelli, Alex J. Berkowitz, Daniel W. Zuschlag

et al.

Tetrahedron, Journal Year: 2022, Volume and Issue: 130, P. 133175 - 133175

Published: Dec. 1, 2022

Language: Английский

Citations

19
Electrochemical Site‐Selective Alkylation of Tropones via Formal C(sp3)−C(sp2) Coupling Reaction DOI Creative Commons
Andrea Brunetti,

Mauro Garbini,

Nico G. Kub

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(9), P. 1965 - 1971

Published: March 5, 2024

Abstract The first site‐selective electrochemical alkylation of tropones is realized by reacting 2‐acetoxytropones and redox‐active‐esters (RAEs). electroreductive protocol enables the preparation mono‐ disubstituted in high yields (up to 71%) under very mild conditions. Dedicated voltammetric measurements served for identification as a class valuable trapping agents nucleophilic radical species shed light on whole mechanistic profile. Wide tolerance towards functional groups (27 examples) application late‐stage functionalization bioactive compound ( i. e . Colchicine analogue), emphasize synthetic impact present methodology.

Language: Английский

Citations

4
Studies Concerned with the Structure and Synthesis of the Anti‐viral Tropolone Glycoside Liriosmaside A DOI Creative Commons
Qi Chen,

Yaping Zhan,

Michael G. Gardiner

et al.

ChemistryOpen, Journal Year: 2025, Volume and Issue: unknown

Published: April 8, 2025

Abstract A bromotropone corresponding to the agylcone of glycosylated sesquiterpenoid natural product liriosmaside has been prepared over ten steps and in a fully regio‐controlled manner through gem ‐dibromocyclopropane‐mediated ring‐expansion readily accessible decalenone. Pd[0]‐mediated glucosylation reaction applied this afforded mixture from which an enantiomerically pure cross‐coupling could be obtained its structure confirmed single‐crystal X‐ray analysis derivative. Various (unsuccessful) attempts are described selectively acylate last compound thereby install 3‐hydroxy‐3‐methylglutaric acid or HMGA‐containing side chain title product. literature survey other products embodying HMGA motif suggest that co‐metabolite B S ‐configured at C3”. The evaluation glucosylated tropone series anti‐bacterial, anti‐fungal cytotoxicity assays reveals it is inactive all these so emphasizing prospect related troponoids, including B, can serve as useful models for new anti‐viral agents.

Language: Английский

Citations

0
Visible-light-mediated site-selective C(sp2)–H alkylation of tropones facilitates semi-synthesis of cephafortunoids A and B DOI Creative Commons
Q. Zeng, Cheng‐Yu Zheng,

Zhan‐Peng Ge

et al.

Chemical Science, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

An efficient visible-light-driven method for achieving α-site-selective C–H alkylation of tropones was developed. It applied to transform fortunolide A into cephafortunoids and B, marking the first synthesis C 20 Cephalotaxus troponoids.

Language: Английский

Citations

0
Troponoid Compounds as Therapeutic Agents and as Targets and Templates for Chemical Synthesis DOI
Martin G. Banwell, Shen Tan, Qi Chen

et al.

Synlett, Journal Year: 2022, Volume and Issue: 33(20), P. 1968 - 1990

Published: Aug. 16, 2022

Abstract The renewed interest in troponoid compounds as potential therapeutic agents and the ongoing discovery of new, naturally occurring biologically active members class has resulted an attendant focus on developing deploying methods for their synthesis. This account highlights some significant recent developments area chemistry that serve to contextualize our group’s longstanding synthesis such through cyclopropane-mediated ring-expansion cyclohexanoid benzenoid compounds. various means by which conversions can be accomplished application both natural non-natural troponoids are detailed. 1 Introduction 2 Naturally Occurring Troponoid Compounds Their Biogenesis 3 Medicinal Chemistry Aspects 4 Troponoids Materials Science 5 Scaffolds Chemical Synthesis 6 An Overview Methods Available Preparing 7 Cyclopropane-Mediated Ring-Expansion Reactions Leading 8 Conclusions

Language: Английский

Citations

13
The Palladium-Catalyzed Glycosylation of Halotropones DOI
Qi Chen, Ping Lan, Shen Tan

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(2), P. 384 - 388

Published: Jan. 6, 2023

A range of mono- and disaccharides, including glucose derivative 10, has been cleanly coupled, in the presence a Pd catalyst, with various halogenated structurally distinctive tropones, "parent" compound 11, to afford corresponding α- β-anomeric forms tropolone glycosides, e.g., 12 13, respectively. Varying ligand used influences anomer distribution significantly such that either or β-form predominates. Notable chemo- regioselectivities are observed when dihalogenated troponoids employed as coupling partners.

Language: Английский

Citations

8