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A Formal Synthesis of Porantheridine and an Epimer.

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Title: A Formal Synthesis of Porantheridine and an Epimer.
Authors: Bates, Roderick W.1 roderick@ntu.edu.sg, Lu, Yongna1
Source: Journal of Organic Chemistry. 12/18/2009, Vol. 74 Issue 24, p9460-9465. 6p.
Subjects: Organic synthesis, Piperidine, Silver catalysts, Ring formation (Chemistry), Stereochemistry, X-ray crystallography, Allene
Abstract: A formal synthesis of porantheridine and a synthesis of its C6-epimer have been completed, employing silver-catalyzed allene cyclization to form a common cis-tsoxazolidine intermediate and related N-acyl iminium ion intermediates for side-chain introduction. The stereochemistry of this step can be controlled by choice of the N-protection method. [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: 47248136
AccessLevel: 6
PubType: Academic Journal
PubTypeId: academicJournal
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  Data: A Formal Synthesis of Porantheridine and an Epimer.
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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="%22Lu%2C+Yongna%22">Lu, Yongna</searchLink><relatesTo>1</relatesTo>
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  Data: <searchLink fieldCode="JN" term="%22Journal+of+Organic+Chemistry%22">Journal of Organic Chemistry</searchLink>. 12/18/2009, Vol. 74 Issue 24, p9460-9465. 6p.
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  Data: <searchLink fieldCode="DE" term="%22Organic+synthesis%22">Organic synthesis</searchLink><br /><searchLink fieldCode="DE" term="%22Piperidine%22">Piperidine</searchLink><br /><searchLink fieldCode="DE" term="%22Silver+catalysts%22">Silver catalysts</searchLink><br /><searchLink fieldCode="DE" term="%22Ring+formation+%28Chemistry%29%22">Ring formation (Chemistry)</searchLink><br /><searchLink fieldCode="DE" term="%22Stereochemistry%22">Stereochemistry</searchLink><br /><searchLink fieldCode="DE" term="%22X-ray+crystallography%22">X-ray crystallography</searchLink><br /><searchLink fieldCode="DE" term="%22Allene%22">Allene</searchLink>
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  Label: Abstract
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  Data: A formal synthesis of porantheridine and a synthesis of its C6-epimer have been completed, employing silver-catalyzed allene cyclization to form a common cis-tsoxazolidine intermediate and related N-acyl iminium ion intermediates for side-chain introduction. The stereochemistry of this step can be controlled by choice of the N-protection method. [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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RecordInfo BibRecord:
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    Identifiers:
      – Type: doi
        Value: 10.1021/jo9021925
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      – Code: eng
        Text: English
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        PageCount: 6
        StartPage: 9460
    Subjects:
      – SubjectFull: Organic synthesis
        Type: general
      – SubjectFull: Piperidine
        Type: general
      – SubjectFull: Silver catalysts
        Type: general
      – SubjectFull: Ring formation (Chemistry)
        Type: general
      – SubjectFull: Stereochemistry
        Type: general
      – SubjectFull: X-ray crystallography
        Type: general
      – SubjectFull: Allene
        Type: general
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      – TitleFull: A Formal Synthesis of Porantheridine and an Epimer.
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            NameFull: Bates, Roderick W.
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            NameFull: Lu, Yongna
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              Text: 12/18/2009
              Type: published
              Y: 2009
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              Value: 24
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            – TitleFull: Journal of Organic Chemistry
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