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Anguinomycins and derivatives: total syntheses, modeling, and biological evaluation of the inhibition of nucleocytoplasmic transport.(Report)

The synthesis of the polyketide natural products anguinomycin C and D is described based on Negishi stereoinversion cross coupling, Jacobsen Cr(III)-catalyzed Hetero Diels-Alder reaction, Evans B-mediated syn-aldol chemistry and B-alkyl Suzuki-Miyaura cross coupling. Analogues of anguinomycin and le... Full description

Journal Title: Journal of the American Chemical Society Feb 3, 2010, Vol.132(4), p.1432-1442
Main Author: Bonazzi, Simone
Other Authors: Eidam, Oliv , Guttinger, Setphan , Wach, Jean - Yves , Zemp, Ivo , Kutay, Ulrike , Gademann, Karl
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0002-7863
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recordid: gale_ofa220160537
title: Anguinomycins and derivatives: total syntheses, modeling, and biological evaluation of the inhibition of nucleocytoplasmic transport.(Report)
format: Article
creator:
  • Bonazzi, Simone
  • Eidam, Oliv
  • Guttinger, Setphan
  • Wach, Jean - Yves
  • Zemp, Ivo
  • Kutay, Ulrike
  • Gademann, Karl
subjects:
  • Antineoplastic Agents -- Chemical Properties
  • Antineoplastic Agents -- Structure
  • Catalysis -- Analysis
  • Chromium (Metal) -- Chemical Properties
  • Diels-alder Reaction -- Analysis
ispartof: Journal of the American Chemical Society, Feb 3, 2010, Vol.132(4), p.1432-1442
description: The synthesis of the polyketide natural products anguinomycin C and D is described based on Negishi stereoinversion cross coupling, Jacobsen Cr(III)-catalyzed Hetero Diels-Alder reaction, Evans B-mediated syn-aldol chemistry and B-alkyl Suzuki-Miyaura cross coupling. Analogues of anguinomycin and leptomycin B (LMB) are prepared and the simple [alpha],[beta]-unsaturated lactone analogue with a truncated polyketide chain has retained most of the biological activity.
language: English
source:
identifier: ISSN: 0002-7863
fulltext: no_fulltext
issn:
  • 0002-7863
  • 00027863
url: Link


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titleAnguinomycins and derivatives: total syntheses, modeling, and biological evaluation of the inhibition of nucleocytoplasmic transport.(Report)
creatorBonazzi, Simone ; Eidam, Oliv ; Guttinger, Setphan ; Wach, Jean - Yves ; Zemp, Ivo ; Kutay, Ulrike ; Gademann, Karl
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identifierISSN: 0002-7863
subjectAntineoplastic Agents -- Chemical Properties ; Antineoplastic Agents -- Structure ; Catalysis -- Analysis ; Chromium (Metal) -- Chemical Properties ; Diels-alder Reaction -- Analysis
descriptionThe synthesis of the polyketide natural products anguinomycin C and D is described based on Negishi stereoinversion cross coupling, Jacobsen Cr(III)-catalyzed Hetero Diels-Alder reaction, Evans B-mediated syn-aldol chemistry and B-alkyl Suzuki-Miyaura cross coupling. Analogues of anguinomycin and leptomycin B (LMB) are prepared and the simple [alpha],[beta]-unsaturated lactone analogue with a truncated polyketide chain has retained most of the biological activity.
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titleAnguinomycins and derivatives: total syntheses, modeling, and biological evaluation of the inhibition of nucleocytoplasmic transport.(Report)
descriptionThe synthesis of the polyketide natural products anguinomycin C and D is described based on Negishi stereoinversion cross coupling, Jacobsen Cr(III)-catalyzed Hetero Diels-Alder reaction, Evans B-mediated syn-aldol chemistry and B-alkyl Suzuki-Miyaura cross coupling. Analogues of anguinomycin and leptomycin B (LMB) are prepared and the simple [alpha],[beta]-unsaturated lactone analogue with a truncated polyketide chain has retained most of the biological activity.
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titleAnguinomycins and derivatives: total syntheses, modeling, and biological evaluation of the inhibition of nucleocytoplasmic transport.(Report)
authorBonazzi, Simone ; Eidam, Oliv ; Guttinger, Setphan ; Wach, Jean - Yves ; Zemp, Ivo ; Kutay, Ulrike ; Gademann, Karl
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abstractThe synthesis of the polyketide natural products anguinomycin C and D is described based on Negishi stereoinversion cross coupling, Jacobsen Cr(III)-catalyzed Hetero Diels-Alder reaction, Evans B-mediated syn-aldol chemistry and B-alkyl Suzuki-Miyaura cross coupling. Analogues of anguinomycin and leptomycin B (LMB) are prepared and the simple [alpha],[beta]-unsaturated lactone analogue with a truncated polyketide chain has retained most of the biological activity.
pubAmerican Chemical Society
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date2010-02-03