Journal Article10.1021/ACS.ORGLETT.9B00413
Function-Oriented Synthesis toward Peloruside A Analogues
Anne-Caroline Chany,Frédéric Legros,Heloua Haroun,Uday Kumar Kundu,Bohdan Biletskyi,Sergii Torlak,Monique Mathé-Allainmat,Jacques Lebreton,Aurélie Macé,Bertrand Carboni,Brigitte Renoux,Pascal Gosselin,Gilles Dujardin,Catherine Gaulon-Nourry +13 more
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TL;DR: A convergent and rapid synthesis of original C2,C3-unsaturated, C11,C13-keto-enol macrocycles with a peloruside A skeleton with antiproliferative activity in the low micromolar range on NCI and MCF7 tumor cell lines is developed.
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About: This article is published in Organic Letters. The article was published on 12 Mar 2019.
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Citations
Recent ring distortion reactions for diversifying complex natural products.
TL;DR: This work reviews the ring distortion reactions recently used in complexity-to-diversity (CtD) and pseudo natural products (pseudo-NPs) strategies for diversifying complex natural products and provides a toolbox for chemists for the application of ring distort reactions to access natural product-like molecules.
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TIPS-Diazoacetone Aldol Addition: Mechanistic Aspects and Contribution to the Synthesis
Sigrid Gavelle,Imen Abid,Bohdan Biletskyi,Sylvain Henrion,Annie Hémon-Ribaud,Jérôme Lhoste,Arnaud Martel,Gilles Dujardin,Catherine Gaulon-Nourry +8 more
TL;DR: Aldol addition of α-triisopropylsilyl-α-diazoacetone, promoted by excess lithium diisopropylamide (LDA), was developed and applied to the synthesis of original C-TIPS diazoaldols, C- TIPS diazoketols, and a related Mannich-type product as discussed by the authors.
2
Designing new agents for the peloruside binding site
Ethan Woolly
- 25 Mar 2022
TL;DR: In this paper , a guided analogue synthesis of peloruside A was proposed to simplify the structure in a way that still retains the pharmacophores, identified as the side chain and the pyran, while being more synthetically accessible.
The aldol reaction: Group I and II enolates
Dai Viet N. Vo,Hoang‐Phuc Pham,Nhan Do Van Thanh +2 more
- 01 Jan 2024
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•Journal Article
Peloruside A, a Novel Antimitotic Agent with Paclitaxel-like Microtubule- stabilizing Activity
K. A. Hood,Lyndon M. West,Berber Rouwé,Peter T. Northcote,Michael V. Berridge,St. John Wakefield,John H. Miller +6 more
TL;DR: Peloruside A is a novel secondary metabolite isolated from a New Zealand marine sponge that has potent paclitaxel-like microtubule-stabilizing activity and is cytotoxic at nanomolar concentrations.
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TL;DR: The structural analysis illustrates distinct mechanisms of these drugs for stabilizing the MT lattice and is of relevance to the possible use of combinations of MSAs to regulate MT activity and improve therapeutic potential.
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Z-Selective Horner−Wadsworth−Emmons Reaction of α-Substituted Ethyl (Diarylphosphono)acetates with Aldehydes1
TL;DR: In this paper, the temperature-dependent selectivity was observed in the reaction of (PhO)2P(O)CHBuCO2Et with octyl aldehyde.
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