派克霉素的全合成。 - Suppr

Total synthesis of pactamycin.

作者信息

Hanessian Stephen, Vakiti Ramkrishna Reddy, Dorich Stéphane, Banerjee Shyamapada, Lecomte Fabien, DelValle Juan R, Zhang Jianbin, Deschênes-Simard Benoît

机构信息

Department of Chemistry, Université de Montréal, Station Centre Ville, C.P. 6128, Montreal, Qc, H3C 3J7, Canada.

出版信息

Angew Chem Int Ed Engl. 2011 Apr 4;50(15):3497-500. doi: 10.1002/anie.201008079. Epub 2011 Mar 2.

DOI:10.1002/anie.201008079

PMID:21370372

Abstract

摘要

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Strategies for the Syntheses of Pactamycin and Jogyamycin.

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Hidden symmetry enables a 15-step total synthesis of pactamycin.

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Strategies for the Syntheses of Pactamycin and Jogyamycin.

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相似文献

Total synthesis of pactamycin.

Angew Chem Int Ed Engl. 2011 Apr 4;50(15):3497-500. doi: 10.1002/anie.201008079. Epub 2011 Mar 2.

Synthesis of the oxygenated pactamycin core.

Org Lett. 2007 Mar 29;9(7):1359-62. doi: 10.1021/ol0702472. Epub 2007 Mar 6.

Total synthesis of pactamycin and pactamycate: a detailed account.

J Org Chem. 2012 Nov 2;77(21):9458-72. doi: 10.1021/jo301638z. Epub 2012 Oct 19.

Access to the pactamycin core via an epoxide opening cascade.

Org Lett. 2012 Jul 20;14(14):3632-5. doi: 10.1021/ol301461e. Epub 2012 Jul 3.

Total Synthesis of Pactalactam, an Imidazolidinone-Type Pactamycin Analogue.

Org Lett. 2019 May 17;21(10):3554-3557. doi: 10.1021/acs.orglett.9b00905. Epub 2019 May 6.

Enantioselective synthesis of pactamycin, a complex antitumor antibiotic.

Science. 2013 Apr 12;340(6129):180-2. doi: 10.1126/science.1234756.

Asymmetric Synthesis and Biological Activities of Pactamycin-Inspired Aminocyclopentitols.

Org Lett. 2018 Jan 19;20(2):397-400. doi: 10.1021/acs.orglett.7b03681. Epub 2018 Jan 10.

Chemical Modification of Pactamycin Leads to New Compounds with Retained Antimicrobial Activity and Reduced Toxicity.

Molecules. 2024 Sep 3;29(17):4169. doi: 10.3390/molecules29174169.

Strategies for the Syntheses of Pactamycin and Jogyamycin.

Angew Chem Int Ed Engl. 2021 Jun 21;60(26):14252-14271. doi: 10.1002/anie.202004560. Epub 2021 Jan 18.

Hidden symmetry enables a 15-step total synthesis of pactamycin.

Angew Chem Int Ed Engl. 2013 Oct 4;52(41):10694-6. doi: 10.1002/anie.201305464. Epub 2013 Aug 22.

引用本文的文献

Reactivity of Anomalous Aziridines for Versatile Access to High Fsp Amine Chemical Space.

Acc Chem Res. 2025 Jan 21;58(2):231-249. doi: 10.1021/acs.accounts.4c00670. Epub 2024 Dec 30.

Chemical Modification of Pactamycin Leads to New Compounds with Retained Antimicrobial Activity and Reduced Toxicity.

Molecules. 2024 Sep 3;29(17):4169. doi: 10.3390/molecules29174169.

Visible Light Promoted [3+2]-Cycloaddition for the Synthesis of Cyclopenta[]chromenocarbonitrile Derivatives.

J Org Chem. 2023 Dec 1;88(23):16589-16597. doi: 10.1021/acs.joc.3c02172. Epub 2023 Nov 21.

Progress toward the Total Synthesis of Jogyamycin Using a Tandem Ichikawa/Winstein Rearrangement.

Org Lett. 2023 Nov 24;25(46):8279-8283. doi: 10.1021/acs.orglett.3c03286. Epub 2023 Nov 9.

Strategies for the Syntheses of Pactamycin and Jogyamycin.

Angew Chem Int Ed Engl. 2021 Jun 21;60(26):14252-14271. doi: 10.1002/anie.202004560. Epub 2021 Jan 18.

Oxidative allene amination for the synthesis of nitrogen-containing heterocycles.

ARKIVOC. 2018;2018:204-233. doi: 10.24820/ark.5550190.p010.670. Epub 2018 Nov 26.

Stereocontrolled Synthesis of the Aminocyclopentitol Core of Jogyamycin via an Ichikawa Rearrangement Reaction.

J Org Chem. 2019 Nov 1;84(21):14092-14100. doi: 10.1021/acs.joc.9b02249. Epub 2019 Oct 16.

Enantioselective PCCP Brønsted acid-catalyzed aza-Piancatelli rearrangement.

Beilstein J Org Chem. 2019 Jul 12;15:1569-1574. doi: 10.3762/bjoc.15.160. eCollection 2019.

Fixing the Unfixable: The Art of Optimizing Natural Products for Human Medicine.

J Med Chem. 2019 Sep 26;62(18):8412-8428. doi: 10.1021/acs.jmedchem.9b00246. Epub 2019 Apr 26.

Asymmetric synthesis of cyclopentanes bearing four contiguous stereocenters via an NHC-catalyzed Michael/Michael/esterification domino reaction.

Chem Commun (Camb). 2016 Feb 11;52(12):2609-11. doi: 10.1039/c5cc09581f. Epub 2016 Jan 11.

Total synthesis of pactamycin.

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