Stereoselective Total Synthesis of (–)–6–epi–Hygrophorone B14 and (–)–4–epi–Hygrophorone D14

Surender, Banothu; Vinaykumar, Allam; Kumar, Bejugam Santhosh; Vemulapalli, Sahithya Phani Babu; Rao, B. Venkateswara

doi:10.1002/slct.201801621

Cited by 4 publications

(1 citation statement)

References 23 publications

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“…Rao and co-workers described the stereoselective total synthesis of (À )-4-epi-hygrophorone D 298 and (À )-6-epihygrophorone B 297 (Scheme 33), [214] these hygrophorones possess cyclopentenone core decorated with different functionalities and possess antibacterial and antifungal activities and also shows the activity toward Gram-positive bacteria. In this strategy, RCM was one of the crucial steps to forge cyclo-pentenone core.…”

Section: Total Synthesis Of Natural Products Based On Rcmmentioning

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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Section: Total Synthesis Of Natural Products Based On Rcmmentioning

confidence: 99%

Metathesis Reactions in Natural Product Fragments and Total Syntheses

et al. 2022

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The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2018

Herndon

2019

Coordination Chemistry Reviews

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Total synthesis and antimicrobial evaluation of (+)-hygrophorone B12 and its analogues

Kamishima

Suzuki

Narita

et al. 2022

Sci Rep

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This paper describes the synthesis and evaluation of lead compounds with a new chemical skeleton that is not found in conventional antimicrobial agents. The biologically attractive cyclopentenoid (+)-hygrophorone B12, isolated from the fruiting bodies of Hygrophorus abieticola, and its analogues were synthesized in a longer linear sequence of twelve steps, starting from a cyclopentenone derivative. This synthesis involved the following crucial steps: (i) oximation of a ketone to stabilize the requisite aldehyde to install a side chain and (ii) coupling of an aldehyde with a side chain to assemble the desired hygrophorone. Then, the antimicrobial activity of these hygrophorones towards clinically relevant bacterial pathogens was evaluated. The results showed that hygrophorone B12 and its analogues are especially effective in preventing the proliferation of gram-positive bacteria. In addition, it was found that some structural features such as the presence of the enone moiety as well as the carbon–carbon triple bond on the hydrocarbon chain were pivotal to increase the antimicrobial activity of hygrophorone B. This study is expected to support the development of novel antimicrobial agents by flexibly synthesizing hygrophorone B analogues with a carbon five-membered ring skeleton from the common intermediate.

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Stereoselective Total Synthesis of (–)–6–epi–Hygrophorone B¹⁴ and (–)–4–epi–Hygrophorone D¹⁴

Abstract: Total synthesis of (–)–6–epi–hygrophorones B14 and (–)–4–epi–hygrophorone D14 was achieved using stereoselective Grignard reaction, Bernet–Vasella protocol and Ring closing metathesis, starting from D–mannose.

Cited by 4 publications

References 23 publications

Metathesis Reactions in Natural Product Fragments and Total Syntheses

Metathesis Reactions in Natural Product Fragments and Total Syntheses

The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2018

Total synthesis and antimicrobial evaluation of (+)-hygrophorone B12 and its analogues

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