Effect of Substituents on the Molecular Shapes of π‐Basic Macrotricyclic Receptors

Lelias, A.; Aubert, Emmanuel; Chambron, Jean‐Claude; Espinosa, Enrique

doi:10.1002/ejoc.200901398

Cited by 3 publications

(1 citation statement)

References 24 publications

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“…Although the brominated resorcinol 23 is commercially available, it can be easily prepared in virtually quantitative yield by treatment of 3,5-dihydroxybenzoic acid ( 22 ) with bromine (Scheme ). The benzoic acid 23 has been converted to the benzylic alcohol 25 through a three-step sequence via the methyl ester, , but it also was possible to accomplish this overall transformation in just two steps by formation of the acyloxyester 24 while concurrently protecting the phenols as MOM ethers, followed by reduction of this intermediate to the desired alcohol 25 . Protection of the benzylic alcohol 25 as the methyl ether 21 proceeded smoothly, and halogen metal exchange followed by treatment with DMF afforded the desired aldehyde 19 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of a Coumarin-Based Analogue of Schweinfurthin F

et al. 2021

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The natural schweinfurthins are stilbenes with significant antiproliferative activity and an uncertain mechanism of action. To obtain a fluorescent analogue with minimal deviation from the natural structure, a coumarin ring system was annulated to the D-ring, creating a new analogue of schweinfurthin F. This stilbene was prepared through a convergent synthesis, with a Horner–Wadsworth–Emmons condensation employed to form the central stilbene olefin. After preparation of a tricyclic phosphonate via a recent and more efficient modification of the classic Arbuzov reaction, condensation was attempted with an appropriately substituted bicyclic aldehyde but the coumarin system did not survive the reaction conditions. When olefin formation preceded generation of the coumarin, the stilbene formation proceeded smoothly and ultimately allowed access to the targeted coumarin-based schweinfurthin analogue. This analogue displayed the desired fluorescence properties along with significant biological activity in the National Cancer Institute’s 60-cell line bioassay, and the pattern of this biological activity mirrored that of the natural product schweinfurthin F. This approach gives facile access to new fluorescent analogues of the natural schweinfurthins and should be applicable to other natural stilbenes as well.

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Section: Resultsmentioning

confidence: 99%