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Scalable total synthesis and biological evaluation of haouamine A and its atropisomer.

A total synthesis of the complex, bent aromatic ring-containing marine alkaloid haouamine A is achieved through a route in which every step (with the exception of the final deprotection) is performed on a gram-scale. This is accomplished through the development of a method for the dehydrogenation of... Full description

Journal Title: Journal of the American Chemical Society July 8, 2009, Vol.131(26), pp.9172-9173
Main Author: Burns, Noah Z
Other Authors: Krylova, Irina N , Hannoush, Rami N , Baran, Phil S
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: E-ISSN: 1520-5126 ; DOI: 1520-5126 ; DOI: 10.1021/ja903745s
Link: http://search.proquest.com/docview/67442812/?pq-origsite=primo
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title: Scalable total synthesis and biological evaluation of haouamine A and its atropisomer.
format: Article
creator:
  • Burns, Noah Z
  • Krylova, Irina N
  • Hannoush, Rami N
  • Baran, Phil S
subjects:
  • Antineoplastic Agents–Chemical Synthesis
  • Cell Line, Tumor–Chemistry
  • Cell Survival–Pharmacology
  • Crystallography, X-Ray–Drug Effects
  • Heterocyclic Compounds, 4 or More Rings–Chemical Synthesis
  • Humans–Chemistry
  • Male–Pharmacology
  • Microbial Sensitivity Tests–Drug Therapy
  • Models, Molecular–Drug Therapy
  • Molecular Structure–Drug Therapy
  • Prostatic Neoplasms–Drug Therapy
  • Stereoisomerism–Drug Therapy
  • Antineoplastic Agents
  • Heterocyclic Compounds, 4 or More Rings
  • Haouamine A
ispartof: Journal of the American Chemical Society, July 8, 2009, Vol.131(26), pp.9172-9173
description: A total synthesis of the complex, bent aromatic ring-containing marine alkaloid haouamine A is achieved through a route in which every step (with the exception of the final deprotection) is performed on a gram-scale. This is accomplished through the development of a method for the dehydrogenation of cyclohexenones that allows for point-to-planar chirality transfer. This strategy makes it possible to program the desired atropisomeric outcome from a simple chiral cyclohexenone. By synthesizing atrop-haouamine A, this work has firmly established that natural haouamine exists as a single, nonequilibrating atropisomer. Finally, biological investigations demonstrate that the bent aromatic ring of this natural product is critical for anticancer activity against PC3 cells.
language: eng
source:
identifier: E-ISSN: 1520-5126 ; DOI: 1520-5126 ; DOI: 10.1021/ja903745s
fulltext: no_fulltext
issn:
  • 15205126
  • 1520-5126
url: Link


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titleScalable total synthesis and biological evaluation of haouamine A and its atropisomer.
creatorBurns, Noah Z ; Krylova, Irina N ; Hannoush, Rami N ; Baran, Phil S
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subjectAntineoplastic Agents–Chemical Synthesis ; Cell Line, Tumor–Chemistry ; Cell Survival–Pharmacology ; Crystallography, X-Ray–Drug Effects ; Heterocyclic Compounds, 4 or More Rings–Chemical Synthesis ; Humans–Chemistry ; Male–Pharmacology ; Microbial Sensitivity Tests–Drug Therapy ; Models, Molecular–Drug Therapy ; Molecular Structure–Drug Therapy ; Prostatic Neoplasms–Drug Therapy ; Stereoisomerism–Drug Therapy ; Antineoplastic Agents ; Heterocyclic Compounds, 4 or More Rings ; Haouamine A
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descriptionA total synthesis of the complex, bent aromatic ring-containing marine alkaloid haouamine A is achieved through a route in which every step (with the exception of the final deprotection) is performed on a gram-scale. This is accomplished through the development of a method for the dehydrogenation of cyclohexenones that allows for point-to-planar chirality transfer. This strategy makes it possible to program the desired atropisomeric outcome from a simple chiral cyclohexenone. By synthesizing atrop-haouamine A, this work has firmly established that natural haouamine exists as a single, nonequilibrating atropisomer. Finally, biological investigations demonstrate that the bent aromatic ring of this natural product is critical for anticancer activity against PC3 cells.
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