Structure Confirmation of a Bioactive Lactone Isolated from Otoba parvifolia through the Synthesis of a Model Compound

Marques, Francisco A.; Lenz, Cesar A.; Simonelli, Fábio; Maia, Beatriz Helena L. N. Sales; Vellasco, and Adriana P.; Eberlin, Marcos N.

doi:10.1021/np049771x

Cited by 14 publications

(9 citation statements)

References 10 publications

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“…The reaction was also compatible with an alkyl group on the 2-cyclohexene-1-one nucleus. The reaction of 6-methyl-2-cyclohexen-1-one ( 1g ) with 2a afforded 2-methyl-4-( para -tolyl)phenol ( 3ga ) in 47% yield (entry 7). When 5-bromo- meta -xylene ( 2b ) was used as an aryl bromide, the corresponding biaryl was obtained in 60% yield (entry 8).…”

mentioning

confidence: 99%

An Alternative Approach to para-C–H Arylation of Phenol: Palladium-Catalyzed Tandem γ-Arylation/Aromatization of 2-Cyclohexen-1-one Derivatives

et al. 2012

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confidence: 99%

An Alternative Approach to para-C–H Arylation of Phenol: Palladium-Catalyzed Tandem γ-Arylation/Aromatization of 2-Cyclohexen-1-one Derivatives

et al. 2012

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“…7a and Supplementary Table 11 )). It is worth mentioning that, oxocane architecture exists as the core scaffold in compounds possessing significant biological activities 35 , 36 . Employing the same conditions to substituted aniline derivatives allowed for the synthesis of compounds 22b , 22c , and 22d in good yields and complete diastereo-control.…”

Section: Resultsmentioning

confidence: 99%

Multidirectional desymmetrization of pluripotent building block en route to diastereoselective synthesis of complex nature-inspired scaffolds

et al. 2018

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Octahydroindolo[2,3-a]quinolizine ring system forms the basic framework comprised of more than 2000 distinct family members of natural products. Despite the potential applications of this privileged substructure in drug discovery, efficient, atom-economic and modular strategies for its assembly, is underdeveloped. Here we show a one-step build/couple/pair strategy that uniquely allows access to diverse octahydroindolo[2,3-a]quinolizine scaffolds with more than three contiguous chiral centers and broad distribution of molecular shapes via desymmetrization of the oxidative-dearomatization products of phenols. The cascade demonstrates excellent diastereoselectivity, and the enantioselectivity exceeded 99% when amino acids are used as chiral reagents. Furthermore, two diastereoselective reactions for the synthesis of oxocanes and piperazinones, is reported. Phenotypic screening of the octahydroindolo[2,3-a]quinolizine library identifies small molecule probes that selectively suppress mitochondrial membrane potential, ATP contents and elevate the ROS contents in hepatoma cells (Hepa1–6) without altering the immunological activation or reprogramming of T- and B-cells, a promising approach to cancer therapy.

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“…A soln. of 6‐methyl‐2‐cyclohexenone (0.36 g, 3.3 mmol, 1 equiv.) in HMPA (1.00 ml) was added dropwise to a THF soln.…”

Section: Methodsmentioning

confidence: 99%

Ruthenium Lewis Acid‐Catalyzed Asymmetric Diels–Alder Reactions: Reverse‐Face Selectivity for α,β‐Unsaturated Aldehydes and Ketones

Thamapipol

Ludwig

Besnard

et al. 2016

Helvetica Chimica Acta

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Acrolein, methacrolein, methyl vinyl ketone, ethyl vinyl ketone, 3-methyl-3-en-2-one, and divinyl ketone were coordinated to a cationic cyclopentadienyl ruthenium(II) Lewis acid incorporating the electron-poor bidentate BIPHOP-F ligand. Analysis by NOESY and ROESY NMR techniques allowed the determination of conformations of enals and enones present in solution in CD 2 Cl 2 . The results were compared to solid-state structures and to the facial selectivities of catalytic asymmetric Diels-Alder reactions with cyclopentadiene. X-Ray structures of four Ru-enal and Ru-enone complexes show the a,b-unsaturated C=O compounds to adopt an anti-s-trans conformation. In solution, enals assume both anti-s-trans and anti-s-cis conformations. An additional conformation, syn-s-trans, is present in enone complexes. Enantioface selectivity in the cycloaddition reactions differs for enals and enones. Reaction products indicate enals to react exclusively in the anti-s-trans conformation, whereas with enones, the major product results from the syn-s-trans conformation. The alkene in s-cis conformations, while present in solution, is shielded and cannot undergo cycloaddition. A syn-s-trans conformation is found in the solid state of the bulky 6,6-dimethyl cyclohexanone-Ru(II) complex. The X-ray structure of divinyl ketone is unique in that the Ru(II) center binds the enone via a g 2 bond to one of the alkene moieties. In solution, coordination to Ru-C=O oxygen is adopted. A comparison of facial preference is also made to the corresponding indenyl Lewis acids.

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Structure Confirmation of a Bioactive Lactone Isolated from Otoba parvifolia through the Synthesis of a Model Compound

Abstract: Synthesis of a model compound 4 structurally related to a bioactive lactone 3 isolated from Otoba parvifolia has been accomplished. The good match between the NMR data of both compounds suggests they have identical bicyclic [3.3.1] carbon skeletons.

Cited by 14 publications

References 10 publications

An Alternative Approach to para-C–H Arylation of Phenol: Palladium-Catalyzed Tandem γ-Arylation/Aromatization of 2-Cyclohexen-1-one Derivatives

An Alternative Approach to para-C–H Arylation of Phenol: Palladium-Catalyzed Tandem γ-Arylation/Aromatization of 2-Cyclohexen-1-one Derivatives

Multidirectional desymmetrization of pluripotent building block en route to diastereoselective synthesis of complex nature-inspired scaffolds

Ruthenium Lewis Acid‐Catalyzed Asymmetric Diels–Alder Reactions: Reverse‐Face Selectivity for α,β‐Unsaturated Aldehydes and Ketones

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