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Synthesis of the Stenine Ring System from Pyrrole.

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Title: Synthesis of the Stenine Ring System from Pyrrole.
Authors: Bates, Roderick W.1 roderick@ntu.edu.sg, Sridhar, S.1
Source: Journal of Organic Chemistry. 6/17/2011, Vol. 76 Issue 12, p5026-5035. 5p. 5 Charts.
Subjects: Organic field-effect transistors, Ring formation (Chemistry), Chemical reactions, Pyrroles, Chemical reduction, Alkenes
Abstract: The skeleton of the stemona alkaloid, stenine, has been synthesized starting from pyrrole, employing an asymmetric organocatalyzed cyclization, Sonogashira coupling, a diastereoselective intramolecular propargylic Barbier reaction, cyclocarbonylation, and diastereoselective alkene reduction. Modulation of the electron-rich nature of the pyrrole nucleus by employing an α-trifluoroacetyl group is essential. The α-trifluoroacetyl group may be rapidly removed under carefully defined, mild conditions. [ABSTRACT FROM AUTHOR]
Copyright of Journal of Organic Chemistry is the property of American Chemical Society and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
Database: Engineering Source
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Header DbId: egs
DbLabel: Engineering Source
An: 62005270
AccessLevel: 6
PubType: Academic Journal
PubTypeId: academicJournal
PreciseRelevancyScore: 0
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  Data: Synthesis of the Stenine Ring System from Pyrrole.
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  Data: <searchLink fieldCode="AR" term="%22Bates%2C+Roderick+W%2E%22">Bates, Roderick W.</searchLink><relatesTo>1</relatesTo><i> roderick@ntu.edu.sg</i><br /><searchLink fieldCode="AR" term="%22Sridhar%2C+S%2E%22">Sridhar, S.</searchLink><relatesTo>1</relatesTo>
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  Data: <searchLink fieldCode="JN" term="%22Journal+of+Organic+Chemistry%22">Journal of Organic Chemistry</searchLink>. 6/17/2011, Vol. 76 Issue 12, p5026-5035. 5p. 5 Charts.
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  Data: <searchLink fieldCode="DE" term="%22Organic+field-effect+transistors%22">Organic field-effect transistors</searchLink><br /><searchLink fieldCode="DE" term="%22Ring+formation+%28Chemistry%29%22">Ring formation (Chemistry)</searchLink><br /><searchLink fieldCode="DE" term="%22Chemical+reactions%22">Chemical reactions</searchLink><br /><searchLink fieldCode="DE" term="%22Pyrroles%22">Pyrroles</searchLink><br /><searchLink fieldCode="DE" term="%22Chemical+reduction%22">Chemical reduction</searchLink><br /><searchLink fieldCode="DE" term="%22Alkenes%22">Alkenes</searchLink>
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  Data: The skeleton of the stemona alkaloid, stenine, has been synthesized starting from pyrrole, employing an asymmetric organocatalyzed cyclization, Sonogashira coupling, a diastereoselective intramolecular propargylic Barbier reaction, cyclocarbonylation, and diastereoselective alkene reduction. Modulation of the electron-rich nature of the pyrrole nucleus by employing an α-trifluoroacetyl group is essential. The α-trifluoroacetyl group may be rapidly removed under carefully defined, mild conditions. [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
  Label:
  Group: Ab
  Data: <i>Copyright of Journal of Organic Chemistry is the property of American Chemical Society and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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        Value: 10.1021/jo200699k
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      – Code: eng
        Text: English
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        PageCount: 5
        StartPage: 5026
    Subjects:
      – SubjectFull: Organic field-effect transistors
        Type: general
      – SubjectFull: Ring formation (Chemistry)
        Type: general
      – SubjectFull: Chemical reactions
        Type: general
      – SubjectFull: Pyrroles
        Type: general
      – SubjectFull: Chemical reduction
        Type: general
      – SubjectFull: Alkenes
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      – TitleFull: Synthesis of the Stenine Ring System from Pyrrole.
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              Text: 6/17/2011
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              Y: 2011
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