A Chemoenzymatic, Enantioconvergent, Asymmetric Total Synthesis of(<i>R</i>)‐Fridamycin E

Ueberbacher, Bernhard J.; Osprian, Ingrid; Mayer, Sandra F.; Faber, Kurt

doi:10.1002/ejoc.200400720

Cited by 23 publications

(16 citation statements)

References 19 publications

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“…Furthermore, the 1 H and 13 C NMR data of 2 could be thoroughly assigned by comparing with spectroscopic data for grincamycin B (1) and previously reported congeners. 19,20 Consequently, the structure of 2 was solved and named grincamycin C.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Cytotoxic Angucycline Class Glycosides from the Deep Sea Actinomycete Streptomyces lusitanus SCSIO LR32

et al. 2012

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Five new C-glycoside angucyclines, named grincamycins B−F (1−5), and a known angucycline antibiotic, grincamycin (6), were isolated from Streptomyces lusitanus SCSIO LR32, an actinomycete of deep sea origin. The structures of these compounds were elucidated on the basis of extensive spectroscopic analyses, including MS and 1D and 2D NMR experiments. All compounds except grincamycin F (5) exhibited in vitro cytotoxicities against the human cancer cell lines HepG2, SW-1990, HeLa, NCI-H460, and MCF-7 and the mouse melanoma cell line B16, with IC 50 values ranging from 1.1 to 31 μM.

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Section: ■ Results and Discussionmentioning

confidence: 99%

“…Compound 20 . From the characteristic absorption bands at 222, 302, and 511 nm in the UV spectrum, as well as the established molecular formula, 5 was determined to be a member of the angucycline class of antibiotics.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Cytotoxic Angucycline Class Glycosides from the Deep Sea Actinomycete Streptomyces lusitanus SCSIO LR32

et al. 2012

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“…The anthraquinone group is a basic part of a large number of organic molecules, biological compounds, and supramolecular systems with application in several fields. For example, various 9,10‐anthraquinone derivatives have been investigated and applied as antitumor agents , antibiotics , pigments in dyestuff , and photoactive chemosensors , as well as used in synthesis of various crown ethers .…”

Section: Introductionmentioning

confidence: 99%

Rapid, Eco‐friendly, and One‐pot Synthesis of New Lariat Ethers Based on Anthraquinone by Using ZnO Nanoparticles via “Mannich” Reaction under Solvent‐free Condition

Sharghi

Khoshnood

Doroodmand

et al. 2015

Journal of Heterocyclic Chem

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High yielding preparation of structurally different anthraquinone lariat ethers from the reaction of a novel anthraquinone aza crown ether 3 with a variety of substituted phenols and paraformaldehyde in the presence of zinc oxide nanoparticles at 100°C in a solvent‐free condition has been described. The procedure of these reactions is very simple, the yields are generally high to excellent, and the method is applicable to large scale operation without any problem. Furthermore, the zinc oxide nanoparticles could be recovered and recycled up to five times by simple filtration of the reaction mixture.

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“…3b,c, 9 While these approaches vary in terms of overall efficiency, the routes all suffered in how asymmetry was introduced into the molecule. These methods varied from the use of chiral starting materials (( S )-lactic acid) 3b and auxiliaries (menthol based titanium enolate) 9a,b to the use of enzymatic (lipase and hydrolase) 3c,9c catalyzed kinetic resolutions. The most recent and arguably most successful of these routes was the one developed by Faber, who utilized a resolution of a rac -2,2-disubstituted epoxide to install the asymmetry of ( R )-fridamycin E (84% ee ).…”

mentioning

confidence: 99%

“…The most recent and arguably most successful of these routes was the one developed by Faber, who utilized a resolution of a rac -2,2-disubstituted epoxide to install the asymmetry of ( R )-fridamycin E (84% ee ). 9c Despite the success of these previous approaches, we felt a catalytic asymmetric approach had the potential for making the synthesis more efficient as well as providing access to either enantiomer for future synthetic and biological studies ( vide infra ). Herein, we describe our development of a new enantio-divergent route to natural ( R )-fridamycin E and unnatural ( S )-fridamycin E that uses the Sharpless dihydroxylation to install asymmetry and our initial evaluation of these enantiomers and antimicrobial agents.…”

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confidence: 99%

De Novo Asymmetric Synthesis of Fridamycin E

et al. 2011

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A de novo asymmetric synthesis of (R)- and (S)-fridamycin E has been achieved. The entirely linear route required only nine steps from commercially available starting materials (16% overall yield). Key transformations included a Claisen rearrangement, a Sharpless dihydroxylation and a cobalt-catalyzed epoxide carbonylation to give a β-lactone intermediate. Antibacterial activities were determined for both enantiomers using two strains of E. coli, with the natural (R)-enantiomer showing significant inhibition against a Gram-(+)-like imp strain (MIC = 8 μM).

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A Chemoenzymatic, Enantioconvergent, Asymmetric Total Synthesis of(R)‐Fridamycin E

Cited by 23 publications

References 19 publications

Cytotoxic Angucycline Class Glycosides from the Deep Sea Actinomycete Streptomyces lusitanus SCSIO LR32

Cytotoxic Angucycline Class Glycosides from the Deep Sea Actinomycete Streptomyces lusitanus SCSIO LR32

Rapid, Eco‐friendly, and One‐pot Synthesis of New Lariat Ethers Based on Anthraquinone by Using ZnO Nanoparticles via “Mannich” Reaction under Solvent‐free Condition

De Novo Asymmetric Synthesis of Fridamycin E

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