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Synthesis, molecular editing, and biological assessment of the potent cytotoxin leiodermatolide.(Report)

The article describes the development of a scalableroute of 19 steps (longest linear sequence) for the sysnthesis of leiodermatolide (1). The synthetic route features a catalytic asymmetric propargylation of a highly enolizable beta-keto-lactone, a ring closing alkyne metathesis and a modified Still... Full description

Journal Title: Journal of the American Chemical Society Nov 5, Vol.136(44), pp.15719-15729
Main Author: Mailhol, Damien
Other Authors: Willwacher, Jens
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0002-7863
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recordid: gale_ofa399802928
title: Synthesis, molecular editing, and biological assessment of the potent cytotoxin leiodermatolide.(Report)
format: Article
creator:
  • Mailhol, Damien
  • Willwacher, Jens
subjects:
  • Cytokinins – Chemical Properties
  • Cytokinins – Research
  • Antineoplastic Agents – Research
  • Antineoplastic Agents – Chemical Properties
ispartof: Journal of the American Chemical Society, Nov 5, Vol.136(44), pp.15719-15729
description: The article describes the development of a scalableroute of 19 steps (longest linear sequence) for the sysnthesis of leiodermatolide (1). The synthetic route features a catalytic asymmetric propargylation of a highly enolizable beta-keto-lactone, a ring closing alkyne metathesis and a modified Stille coupling as the key transformations. Deliberate digression from this robust method allowed a first set of analogues into reach, which allowed the lead qualities of 1 to be assessed; 1 was found to be a potent cytotoxin in human tumor cell proliferation assays.
language: eng
source:
identifier: ISSN: 0002-7863
fulltext: no_fulltext
issn:
  • 0002-7863
  • 00027863
url: Link


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titleSynthesis, molecular editing, and biological assessment of the potent cytotoxin leiodermatolide.(Report)
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subjectCytokinins – Chemical Properties ; Cytokinins – Research ; Antineoplastic Agents – Research ; Antineoplastic Agents – Chemical Properties
descriptionThe article describes the development of a scalableroute of 19 steps (longest linear sequence) for the sysnthesis of leiodermatolide (1). The synthetic route features a catalytic asymmetric propargylation of a highly enolizable beta-keto-lactone, a ring closing alkyne metathesis and a modified Stille coupling as the key transformations. Deliberate digression from this robust method allowed a first set of analogues into reach, which allowed the lead qualities of 1 to be assessed; 1 was found to be a potent cytotoxin in human tumor cell proliferation assays.
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titleSynthesis, molecular editing, and biological assessment of the potent cytotoxin leiodermatolide.(Report)
descriptionThe article describes the development of a scalableroute of 19 steps (longest linear sequence) for the sysnthesis of leiodermatolide (1). The synthetic route features a catalytic asymmetric propargylation of a highly enolizable beta-keto-lactone, a ring closing alkyne metathesis and a modified Stille coupling as the key transformations. Deliberate digression from this robust method allowed a first set of analogues into reach, which allowed the lead qualities of 1 to be assessed; 1 was found to be a potent cytotoxin in human tumor cell proliferation assays.
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abstractThe article describes the development of a scalableroute of 19 steps (longest linear sequence) for the sysnthesis of leiodermatolide (1). The synthetic route features a catalytic asymmetric propargylation of a highly enolizable beta-keto-lactone, a ring closing alkyne metathesis and a modified Stille coupling as the key transformations. Deliberate digression from this robust method allowed a first set of analogues into reach, which allowed the lead qualities of 1 to be assessed; 1 was found to be a potent cytotoxin in human tumor cell proliferation assays.
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atitleSynthesis, molecular editing, and biological assessment of the potent cytotoxin leiodermatolide.
volume136
issue44
issn0002-7863
pubAmerican Chemical Society
pages15719-15729
doi10.1021/ja508846g
eissn15205126
date2014-11-05