A Diastereoselective Route to <i>trans</i>‐2‐Aryl‐2,3‐dihydrobenzofurans through Sequential Cross‐Metathesis/Isomerization/Allylboration Reactions: Synthesis of Bioactive Neolignans

Hemelaere, Rémy; Carreaux, François; Carboni, Bertrand

doi:10.1002/ejoc.201500019

Cited by 28 publications

(15 citation statements)

References 88 publications

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“…Mitsunobu cyclization followed by oxidative cleavage of the alkene and subsequent reduction with simultaneous global deprotection furnished dihydrodehydrodiconiferyalcohol in 60% overall yield, >95:5 dr and 93:7 er, accomplishing a much more e cient and stereoselective synthesis than previously reported (9 steps, 23% overall yield, >95:5 dr, 93:7 er vs. 12 steps, 1.2% overall yield, >95:5 dr, 62:38 er). 69 To gain some preliminary insight into the reaction mechanism, a series of experiments were conducted (Figure 7). Kinetic experiments revealed that in the transformations of allylbenzenes and 1,4-dienes, allylic C-H bond cleavage might not be the rate-determining step.…”

Section: Resultsmentioning

confidence: 99%

Cobalt-Catalyzed Diastereo- and Enantioselective Allyl Addition to Aldehydes and α-Ketoesters through Allylic C–H Functionalization

Zhang

Huang

Meng

2020

Preprint

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Catalytic reactions that can generate nucleophilic allyl–metal intermediates directly from simple alkenes without prefunctionalization, and ones that produce various homoallylic alcohols diastereo- and enantioselectively are of great importance in organic synthesis. Transformations that accomplish these two tasks simultaneously are in high demand, particularly if the catalysts, substrates and reagents are inexpensive and easy to access. Here we report a catalytic process that chemoselective formation of nucleophilic allyl–cobalt complexes through oxidative allylic C–H cleavage of alkenes followed by site-, diastereo- and enantioselective addition to aldehydes and α-ketoesters. The enantioenriched products that are otherwise difficult to access are obtained in up to 96% yield, with >95:5 dr and 98:2 er. The cobalt-based catalyst is derived from a commercially available chiral phosphine ligand. The utility of the method is demonstrated through enantioselective formal synthesis of lithospermic acid and total synthesis of dihydrodehydrodiconiferylalcohol.

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Section: Resultsmentioning

confidence: 99%

Cobalt-Catalyzed Diastereo- and Enantioselective Allyl Addition to Aldehydes and α-Ketoesters through Allylic C–H Functionalization

Zhang

Huang

Meng

2020

Preprint

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“…Borane addition to TS1 followed by alkaline oxidation led to the primary alcohol TS2 in 80%. 28 The hydroxyl group is confirmed in the IR spectrum by the -OH stretch band noticed at 3350 cm -1 and the singlet at d 1.65 ppm in 1 H NMR spectrum. By a reaction of TS2 with mesyl chloride, 29,30 the nucleophilic attack of sodium azide was further favored furnishing the desired alkyl azide TS4.…”

Section: Chemistrymentioning

confidence: 90%

Synthesis and Biological Evaluation of New Eugenol-Derived 1,2,3-Triazoles as Antimycobacterial Agents

Santos

Coelho

Elias

et al. 2019

J. Braz. Chem. Soc.

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Eugenol has diverse biological properties including antimycobacterial activity, and the triazole ring is an important heterocycle in antimycobacterial compounds. Therefore, this research aimed to synthesize novel eugenol-derived 1,2,3-triazole as antimycobacterial agents with interesting cytotoxic profile and pharmacological assets. Sixteen compounds were obtained and characterized by nuclear magnetic resonance (NMR), infrared (IR), and high-resolution mass spectrometry (HRMS). Among them, the best growth inhibition properties from a microdilution assay were observed for three derivatives: a benzylic ether (minimum inhibitory concentration (MIC) = 48.89 µM) against Mycobacterium abscessus (ATCC 19977), an O-galactosyde (MIC = 31.76 µM) against Mycobacterium massiliense (ATCC 48898) and a sulfonate (MIC = 88.64 µM) against Mycobacterium fortuitum (ATCC 6841). They can form biofilms, and the infection progression is challenging to control due to multi-drug resistance profiles against diverse antibiotics. In conclusion, the above-mentioned compounds represent starting points in the search of bioactive molecules against mycobacteria with low cytotoxicity and better pharmacological profiles.

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“…Hemelaere et al. recount the use of a cross‐metathesis/isomerization/allylboration sequence followed by an intramolecular Mitsunobu process for the diastereoselective synthesis of trans ‐2,3‐disubstituted dihydrobenzofurans 156 from diols 155 (Scheme ) …”

Section: Synthetic Routes To Coumaransmentioning

confidence: 99%

Recent Advances in Phthalan and Coumaran Chemistry

et al. 2018

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Oxygen‐containing heterocycles are common in biologically active compounds. In particular, phthalan and coumaran cores are found in pharmaceuticals, organic electronics, and other useful medical and technological applications. Recent research has expanded the methods available for their synthesis. This Minireview presents recent advances in the chemistry of phthalans and coumarans, with the goal of overcoming synthetic challenges and facilitating the applications of phthalans and coumarans.

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A Diastereoselective Route to trans‐2‐Aryl‐2,3‐dihydrobenzofurans through Sequential Cross‐Metathesis/Isomerization/Allylboration Reactions: Synthesis of Bioactive Neolignans

Cited by 28 publications

References 88 publications

Cobalt-Catalyzed Diastereo- and Enantioselective Allyl Addition to Aldehydes and α-Ketoesters through Allylic C–H Functionalization

Cobalt-Catalyzed Diastereo- and Enantioselective Allyl Addition to Aldehydes and α-Ketoesters through Allylic C–H Functionalization

Synthesis and Biological Evaluation of New Eugenol-Derived 1,2,3-Triazoles as Antimycobacterial Agents

Recent Advances in Phthalan and Coumaran Chemistry

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