Synthesis of the alkaloid tyroscherin by an aldol/Curtius strategy

Ugele, Markus; Maier, Martin E.

doi:10.1016/j.tet.2010.02.034

Cited by 17 publications

(6 citation statements)

References 30 publications

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“…4,5 Our motivation was to investigate the structure-activity relationship (SAR) of tyroscherin, followed by efforts to understand its mode of action and IGF-specificity.…”

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confidence: 99%

Total Synthesis and Biological Evaluation of Tyroscherin

et al. 2010

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The efficient synthesis and biological evaluation of both the reported and revised structures of tyroscherin have been achieved. Central to our synthesis is a cross metathesis reaction that generated the trans-olefin regioselectively. This synthetic strategy enabled the facile manipulation of tyroscherin stereochemistry facilitating the generation of all 16 tyroscherin diastereomers and a photoactivatable tyroscherin-based affinity probe for future mode of action studies.

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“…4,5 Our motivation was to investigate the structure-activity relationship (SAR) of tyroscherin, followed by efforts to understand its mode of action and IGF-specificity.…”

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confidence: 99%

Total Synthesis and Biological Evaluation of Tyroscherin

et al. 2010

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“…LiBH 4 Reduction of 21 to Afford Alcohol 22: This was performed using the same procedures described above for the “LiBH 4 reduction of 9 to afford alcohol 10 ” except that 9 was replaced by 21 . Data for 22 (a colorless oil, 263 mg, 1.07 mmol, chromatography using 15:1 PE/EtOAc, 76 % from 21 ): [ α ] D 25 = –2.5 ( c = 1.00, CHCl 3 ) (lit [ α ] D 20 = –2.0 ( c = 1.00, CHCl 3 )). 1 H NMR (500 MHz, CDCl 3 ) δ = 3.50 (dd, J = 10.6, 5.2 Hz, 1H), 3.46–3.39 (m, 2H), 3.37 (dd, J = 9.7, 6.3 Hz, 1H), 1.77–1.66 (m, 2H), 1.60 (s, 1H), 1.44 (dt, J = 13.6, 6.9 Hz, 1H), 0.94 (dd, J = 6.7, 0.7 Hz, 3H), 0.92–0.87 (m, 12H), 0.04 (s, 6H) ppm; 13 C NMR (125 MHz, CDCl 3 ) δ = 68.41, 68.37, 37.43, 33.44, 33.40, 26.10, 18.50, 17.97, 17.85, –5.23 ppm; FT‐IR (film of a concd solution in CH 2 Cl 2 ) ν = 3444, 2956, 2928, 2857, 1471, 1257, 1196, 1095, 1076, 836, 775 cm –1 ; ESI‐MS m/z 247.2 ([M + H] + ); ESI‐HRMS calcd.…”

Section: Methodsmentioning

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Synthesis and Configuration of a p‐Aminoacetophenonic Acid Isolated from Endophyte of the Mangrove Plant Kandel candel

Xiong

Liu

2020

Eur J Org Chem

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Two diastereomers of the title compound were synthesized through an enantioselective route, with the stereogenic center at the C-2 derived from a commercially available reagent and the one at the C-4 installed via Evans asymmetric aldol condensation. By comparison of 1 H and 13 C NMR spectra as well as optical rotation, the configuration of the natural product was as assigned as (-2R,4R). Some interesting issues such as [a

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“…Cancer cells that rely on the insulin‐like growth factor are inhibited by the molecule (IGF). The total synthesis of tyroscherin was attempted by Ugele and Maier [41] . This synthetic approach required a slightly different route because the Evans oxazolidinone could only be acylated with the methyl‐ or benzyl ether.…”

Section: Oxazolidinone Chiral Auxiliaries‐induced Asymmetric Synthesismentioning

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TiCl₄‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

2021

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Nature is incessantly affianced to construct bioactive and structurally intriguing compounds with magnificent three‐dimensional frameworks in the Universe. The inadequacy of these naturally occurring precious compounds prompted several minds of chemists to synthesise them in a laboratory for a thorough evaluation of their medicinal and clinical properties via a structure‐activity relationship study. Finding an optimised methodology to synthesise chiral natural products has always been challenging in synthetic organic chemistry, particularly the formation of asymmetric carbon‐carbon bonds adhering to the existing stereochemistry. In this context, chiral auxiliaries have proven to be effective tools for inducing chirality during the synthesis of chiral molecules. In fact, the chiral auxiliary will allow us to control the synthesis of many enantiomerically pure isomers in natural product synthesis. In this area, the significant contribution of the Evans’ chiral auxiliary in TiCl4‐mediated asymmetric aldol reactions to the installation of known configurations in organic synthetic chemistry motivated us to compile an exhaustive and systematic summary of the relevant research findings published in the last two decades.

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Synthesis of the alkaloid tyroscherin by an aldol/Curtius strategy

Cited by 17 publications

References 30 publications

Total Synthesis and Biological Evaluation of Tyroscherin

Total Synthesis and Biological Evaluation of Tyroscherin

Synthesis and Configuration of a p‐Aminoacetophenonic Acid Isolated from Endophyte of the Mangrove Plant Kandel candel

TiCl₄‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

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Synthesis of the alkaloid tyroscherin by an aldol/Curtius strategy

Cited by 17 publications

References 30 publications

Total Synthesis and Biological Evaluation of Tyroscherin

Total Synthesis and Biological Evaluation of Tyroscherin

Synthesis and Configuration of a p‐Aminoacetophenonic Acid Isolated from Endophyte of the Mangrove Plant Kandel candel

TiCl4‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

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TiCl₄‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis