Enantioselective total synthesis of <font>β</font>-zearalenol from (<i>s</i>)-propylene oxide

Kotla, Ravindar; Murugulla, Adharvana Chari; Ruddarraju, Radhakrishnamraju; Aparna, P.; Donthabakthuni, Shobha; Sridhar, Gattu

doi:10.1080/00397911.2017.1383433

Cited by 4 publications

(4 citation statements)

References 12 publications

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“…In a separate study, Murugullaand's group presented an enantioselective total synthesis of β ‐zearalenol 226 (Scheme 19), [198] an estrogenic mycotoxin with 14‐membered macrolactone framework exhibiting anabolic activity. In their approach, the RCM was utilized in late‐stage to build a 14‐membered macrocyclic core.…”

Section: Ring‐closing Metathesis (Rcm)mentioning

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: Ring‐closing Metathesis (Rcm)mentioning

confidence: 99%

Metathesis Reactions in Natural Product Fragments and Total Syntheses

et al. 2022

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“…[112] (3R),(5R)-5-Hydroxy-de-Omethyl lasiodiplodin 67 comprise 12-membered macrolactone unit with two stereogenic centers (3R,5R) linked to the 1,3dihydroxybenzene ring. [113] A short total synthesis of (3R),(5R)-5-hydroxy-de-O-methyllasiodiplodin and its epimer have been provided from commercially accessible (R)-propylene oxide and Orsellinic acid as starting precursors. The key steps included in the synthesis are Wittig reaction, epoxide ring opening and Yamaguchi macrolactonization.…”

Section: -Membered Macrolidesmentioning

confidence: 99%

“…The key steps included in the synthesis are Wittig reaction, epoxide ring opening and Yamaguchi macrolactonization. [113] The synthesis of target molecules 67 and 67 a was started with the formation of 1,3dithiane segment 66 as a common key intermediate from the commercially accessible Orsellinic acid. In this route, orsellinic acid 62 was transformed into aromatic aldehyde 63.…”

Section: -Membered Macrolidesmentioning

confidence: 99%

“…The latter after several steps afforded the key intermediate 1,3dithiane 66 that was used for the formation of both (3R),(5R)-5hydroxy-de-O-methyllasiodiplodin 67 and (3R),(5S)-5-hydroxyde-O-methyllasiodiplodin 67 a in later steps (Scheme 14) . [113] Balticolid 72, a unique class of bioactive 12-membered macrolides, extracted from the marine fungus belonging to the Ascomycetous species by Shushni et al [115] The structure of balticolid was identified to be (3R,11R), (4E,8E)-3-hydroxy-11methyloxacyclododeca-4,8-diene-1,7-dione. Balticolid 72 shows anti-HSV-1 property.…”

Section: -Membered Macrolidesmentioning

confidence: 99%

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Applications of Wittig Reaction in the Total Synthesis of Natural Macrolides

et al. 2020

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The Wittig reaction involves the synthesis of an alkene via the conversion of an aldehyde or ketone with the already generated ylide from a phosphonium salt. Significantly, when this important name reaction is employed the desired alkenes are constructed via a predictable manner, thus resultant particularly are useful in the total synthesis of natural products and synthetic complex organic compounds with definite geometric isomers, exhibiting diverse biological potencies. In this review we try to highlight the applications of the Wittig reaction as an efficient and attractive strategy in the total synthesis of macrolides from 2008 to 2020.

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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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Enantioselective total synthesis of β-zearalenol from (s)-propylene oxide

Cited by 4 publications

References 12 publications

Metathesis Reactions in Natural Product Fragments and Total Syntheses

Metathesis Reactions in Natural Product Fragments and Total Syntheses

Applications of Wittig Reaction in the Total Synthesis of Natural Macrolides

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

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