Total synthesis of PGF2α and 6,15-diketo-PGF1α and formal synthesis of 6-keto-PGF1α via three-component coupling

Kim, Tae-Hyeong; Lee, Sung Il; Kim, Se-Jin; Shim, Su Yong; Ryu, Do Hyun

doi:10.1016/j.tet.2019.130593

Cited by 7 publications

(3 citation statements)

References 47 publications

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“…In addition, we were also interested to explore how the stereogenicity of the α-side chain affected biological action, and consequently also required access to the (S)-enantiomer of compound 2. It should be noted that several methods for the synthesis of optically active forms of 2 have been reported, [11][12][13][14][15] and in this article, we show how (S)-4-[(tert-butyldimethylsilyl)oxy]cyclopent-2en-1-one (3) [16][17][18][19][20] can be used to prepare both (R)-and (S)-2.…”

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confidence: 74%

“…Since some compounds of the type 1 demonstrated comparable activities to Δ 12,14 -15-deoxy-PGJ 2 in assays relevant to inflammation and ways. [16][17][18][19][20] Since the direct nucleophilic displacement of an activated form of 4-hydroxycyclopentenone is problematic and has scarce literature precedence 21,22 alternative methods for the stereocontrolled construction of 2 were considered. From 3, the ketone was initially converted into alcohol 4 via a Luche reduction.…”

Section: Introductionmentioning

confidence: 99%

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An enantiodivergent synthesis of N-Boc-protected (R)- and (S)-4-amino cyclopent-2-en-1-one

Conway

Evans

2021

Journal of Chemical Research

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Routes are reported for the synthesis of both (1 R)- and (1 S)- tert-butyl-(4-oxocyclopent-2-en-1-yl)carbamate 2. Featuring Mitsunobu reactions with di- tert-butyl iminodicarbonate, both syntheses begin from ( S)-4-[( tert-butyldimethylsilyl)oxy]cyclopent-2-en-1-one (3) and take advantage of the 1,4-cyclopentenyl dioxygenation pattern of this optically active starting material. Thus both (−)- and (+)-2 have been accessed from 3 in an enantiodivergent manner in 11% and 10% overall yield over five and seven reaction steps, respectively.

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confidence: 74%

Section: Introductionmentioning

confidence: 99%

An enantiodivergent synthesis of N-Boc-protected (R)- and (S)-4-amino cyclopent-2-en-1-one

Conway

Evans

2021

Journal of Chemical Research

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“…Remarkably, the asymmetric total synthesis of prostaglandin F 2α 871 (Scheme 136) was revealed from the laboratory of Ryu's group, where CM was employed as one of the crucial steps to synthesize the compound 869 at final stage of their synthetic approach. [317] Three components reaction of cyclopentenone derivative 864 with vinylmagnesium bromide in presence of CuBr • SMe 2 and aldehyde 865 generated a ketone 866, which was then converted to aldehyde 867 in series of steps. Next, cross metathesis between 867 and terminal alkene 868 with the involvement of HG-II catalyst afforded an internal alkene derivaitve 869 in good yield.…”

Section: Reviewmentioning

confidence: 99%

Metathesis Reactions in Natural Product Fragments and Total Syntheses

et al. 2022

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The passion of total‐ and fragments syntheses of natural products always remained one of the top priorities among the synthetic chemists worldwide. Due their curiosity toward the complexity of molecules of living nature and their endeavour to imitate them in laboratory; limitless arrays of natural products have been extracted, architecturally‐elucidated, synthesized, and chronicled by utilizing various synthetic methodologies in different fashions. Frequently, the synthesis of complex natural products proceed with inscrutable synthetic challenges, which can be circumvented either by modification of previously developed synthetic methods or by formulating a new one. In this way, a myriad of powerful synthetic reactions have been developed since the genesis of the logic of chemical synthesis. Amongst them, metathesis tactics discovered unexpectedly in the 1950s (Nobel Prize in 2005), have incredibly influenced and changed the landscape of the art of the total and formal synthesis in the last three A. H. Hoveyda, A. R. Zhugralin, me abruptly as compared to other developed transformations or their modified forms. In this particular review article, we envisioned to report a comprehensive detail of the metathetic tools involved in both total and fragments synthesis of natural products in the years 2018 and 2019 along with an overview of 2017.

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Alkene Cross‐Metathesis Reactions

et al. 2021

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This chapter describes olefin cross‐metathesis (CM) reactions catalyzed by ruthenium, molybdenum, and tungsten complexes and surveys the literature from 1993 through 2020. Cross‐metathesis has been applied to the synthesis of a wide range of functionalized alkenes, including natural and biologically active products. Due to its simplicity and inherit atom economy, CM has found applications in the preparation of fine chemicals and various building blocks, and in transformations of biomass. Tandem reactions involving CM as the key step are also reviewed. Examples discussed in this chapter serve to illustrate how the reactivity of alkene substrates in CM depends on the presence of functional groups and steric congestion in the proximity of the reacting double bonds. A discussion of the mechanism of olefin metathesis is also included.

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Total synthesis of PGF2α and 6,15-diketo-PGF1α and formal synthesis of 6-keto-PGF1α via three-component coupling

Cited by 7 publications

References 47 publications

An enantiodivergent synthesis of N-Boc-protected (R)- and (S)-4-amino cyclopent-2-en-1-one

An enantiodivergent synthesis of N-Boc-protected (R)- and (S)-4-amino cyclopent-2-en-1-one

Metathesis Reactions in Natural Product Fragments and Total Syntheses

Alkene Cross‐Metathesis Reactions

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