Biomimetic total syntheses of baefrutones A–D, baeckenon B, and frutescones A, D–F

2020 ◽  
Vol 18 (6) ◽  
pp. 1135-1139
Author(s):  
Ji-Qin Hou ◽  
Jiang-Hong Yu ◽  
Heng Zhao ◽  
Ying-Ying Dong ◽  
Qiu-Shi Peng ◽  
...  
Keyword(s):  
Michael Addition ◽  
Diels Alder ◽  
Total Syntheses ◽  
Click Reactions ◽  
First Time

Biomimetic total syntheses of the natural tasmanone-based meroterpenoids were achieved for the first time via Michael addition, oxidative [4 + 2] cycloaddition, and water-promoted Diels–Alder click reactions.

A Comparative Study of Thiol-Terminated Surface Modification by Click Reactions: Thiol-yne Coupling versus Thiol-ene Michael Addition

2018 ◽  
Vol 5 (24) ◽  
pp. 1801343 ◽  
Author(s):  
Seyed Mohammad Mahdi Dadfar ◽  
Sylwia Sekula-Neuner ◽  
Vanessa Trouillet ◽  
Michael Hirtz
Keyword(s):  
Surface Modification ◽  
Comparative Study ◽  
Michael Addition ◽  
Click Reactions

Catalyst-Free One-Pot Synthesis of Novel Heteroarylamine Substituted Furo[3,2-c]coumarins

Synlett ◽  
2018 ◽  
Vol 29 (12) ◽  
pp. 1589-1592 ◽  
Author(s):  
Abolfazl Olyaei ◽  
Mahnaz Saraei ◽  
Reyhaneh Khoeiniha
Keyword(s):  
Michael Addition ◽  
Aldol Condensation ◽  
Ring Closure ◽  
Dehydration Reaction ◽  
One Pot ◽  
Catalyst Free ◽  
One Pot Synthesis ◽  
Tandem Process ◽  
First Time

A high-yielding cyclocondensation of 4-hydroxycoumarin, phenylglyoxal monohydrate, and heteroarylamines proceeds without catalysis, which gives novel functionalized furo[3,2-c]coumarins and heteroarylamino alkylation of coumarin products in acetonitrile under reflux, is reported for the first time. This tandem process involves sequentially an aldol condensation, Michael addition, a ring closure, and dehydration reaction.

Uncatalyzed diastereoselective synthesis of alkyliminofurochromone-derived benzylmalononitriles via a three-component cascade reaction: competition between Diels–Alder cycloaddition and Michael addition

2021 ◽  
Author(s):  
Mohammad Bagher Teimouri ◽  
Zahra Mokhtare ◽  
Hamid Reza Khavasi
Keyword(s):  
Michael Addition ◽  
Heterocyclic Ring ◽  
Cascade Reaction ◽  
Diels Alder ◽  
Chemical Bonds ◽  
Diastereoselective Synthesis ◽  
Atom Economy ◽  
One Pot

Three new chemical bonds and three stereogenic centres and one heterocyclic ring were assembled stereoselectively in a convenient high atom-economy one-pot operation.

scholarly journals Stereoselective total syntheses of (±)-sinularene and (±)-5-epi-sinularene: a general intramolecular Diels–Alder approach to tricyclic sesquiterpenes

1985 ◽  
Vol 63 (4) ◽  
pp. 993-995 ◽  
Author(s):  
Kazimierz Antczak ◽  
John F. Kingston ◽  
Alex G. Fallis
Keyword(s):  
Double Bond ◽  
Methyl Ester ◽  
Total Synthesis ◽  
Ring System ◽  
Diels Alder ◽  
Exocyclic Double Bond ◽  
Total Syntheses ◽  
Methyl Group ◽  
Secondary Hydroxyl ◽  
Selective Hydrogenolysis

Stereoselective total synthesis of (±)-sinularene and (±)-5-epi-sinularene are described. The sequence employs a "blocked" cyclopentadiene in which the cyclopropane unit also serves as a latent methyl group. Thus intramolecular [4 + 2] cycloaddition of the substituted methyl spiro[2.4]hepta-4,6-dien-1-yl)-2-pentenoate 11 affords 5-benzyloxy-6-isopropyl-8-carbomethoxytetracyclo[5.4.01,7.02,4.02,9]undec-10-ene (12) which after selective hydrogenolysis generates the tricyclo[4.4.01,6.02,8]decane (sinularene) ring system. Removal of the secondary hydroxyl function (Ph3P/CCl4/CH3CN; H2/Pd/C), reduction of the methyl ester (LiAlH4), and introduction of the exocyclic double bond (acetate pyrolysis, 550 °C) completes the synthesis of (±)-sinularene in 14 steps from cyclopentadiene. A parallel series of reactions employing the isopropyl epimer of 12 affords (±)-5-epi-sinularene.

Total syntheses of ericifolione and analogues via a biomimetic inverse-electron-demand Diels-Alder reaction

2021 ◽  
Author(s):  
Tingting Zhou ◽  
Anquan Zheng ◽  
Luqiong Huo ◽  
Changgeng Li ◽  
Haibo Tan ◽  
...  
Keyword(s):  
Sodium Acetate ◽  
Alder Reaction ◽  
Diels Alder ◽  
Total Syntheses ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
Sterically Hindered ◽  
Electron Demand

Driven by bioinspiration and appreciation of the structure of ericifolione, a biomimetic tautomerization/intermolecular inverse-electron-demand hetero Diels-Alder reaction cascade sequence promoted by sodium acetate to rapidly construct sterically hindered dihydropyran scaffolds...

scholarly journals Enantioselective CuII-Catalyzed Diels-Alder and Michael Addition Reactions in Water Using Bio-Inspired Triazacyclophane-Based Ligands

2011 ◽  
Vol 2011 (9) ◽  
pp. 1714-1720 ◽  
Author(s):  
H. Bauke Albada ◽  
Fiora Rosati ◽  
David Coquière ◽  
Gerard Roelfes ◽  
Rob M. J. Liskamp
Keyword(s):  
Michael Addition ◽  
Diels Alder ◽  
Addition Reactions

scholarly journals SYNTHESIS OF AN AZIDE–THIOL LINKER FOR HETEROGENEOUS POLYMER FUNCTIONALIZATION VIA THE “CLICK” REACTION

2018 ◽  
Vol 55 (1B) ◽  
pp. 152
Author(s):  
Thuy Thu Truong
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Click Reaction ◽  
Proton Nuclear Magnetic Resonance ◽  
Reaction Yield ◽  
Reaction Conditions ◽  
Click Reactions ◽  
Heterogeneous Polymer ◽  
Ft Ir ◽  
First Time ◽  
Layer Chromatography

In this study, the synthesis of a telechelic linker bearing both azide and thiol functional groups was described. The reaction conditions were investigated to optimize the reaction yield. The product was analyzed using thin layer chromatography (TLC) and proton nuclear magnetic resonance (1H NMR). The employment of the obtained azide–thiol linker in heterogeneous polymer “click” functionalization was demonstrated for the first time, which was monitored by an online FT–IR method. The obtained telechelic azide–thiol linker is envisioned to be useful chemical tools to link macromolecular chains via orthogonal click reactions.

scholarly journals Direct observation of o-benzyne formation in photochemical hexadehydro-Diels–Alder (hν-HDDA) reactions

2020 ◽  
Vol 11 (34) ◽  
pp. 9198-9208 ◽  
Author(s):  
Xiaonan Ma ◽  
Jan Maier ◽  
Michael Wenzel ◽  
Alexandra Friedrich ◽  
Andreas Steffen ◽  
...  
Keyword(s):  
Absorption Spectrum ◽  
Direct Observation ◽  
Diels Alder ◽  
Visible Absorption Spectrum ◽  
Visible Absorption ◽  
First Time

We report the transient ultraviolet/visible absorption spectrum of an o-benzyne species in solution for the first time.

Sign in / Sign up

Export Citation Format

Share Document