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Aza-Wacker Cyclization Toward the Bridged Core of FR901483.

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Title: Aza-Wacker Cyclization Toward the Bridged Core of FR901483.
Authors: Shen, Defeng1 (AUTHOR), Xie, Changmin1 (AUTHOR), Ruan, Zhuwei1 (AUTHOR), Yang, Chen1 (AUTHOR), Huang, Sha-Hua2 (AUTHOR), Zhu, Lili1 (AUTHOR), Hong, Ran1 (AUTHOR)
Source: Synthesis. Jun2023, Vol. 55 Issue 12, p1940-1948. 9p.
Subjects: Double bonds, Tertiary amines, Ring formation (Chemistry), Derivatization, Amines
Abstract: A nine-step synthetic route to access the tricyclic core of FR901483 is reported, featuring a key aza-Wacker cyclization step to construct an α-tertiary amine (ATA) in the bridged structure. The aza-Wacker protocol can tolerate both exocyclic and endocyclic double bonds, providing viable access to various bridged bicyclic rings bearing an ATA (e.g., 6-azabicyclo[3.2.1]octane, 7-azabicyclo[3.3.1]nonane, and 7-azabicyclo[4.2.1]nonane) in good to excellent yields. The synthetic studies presented herein enable structural derivatization of FR901483 to further exploit its compelling biological activities. [ABSTRACT FROM AUTHOR]
Copyright of Synthesis is the property of Georg Thieme Verlag Stuttgart 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: 163928318
AccessLevel: 6
PubType: Academic Journal
PubTypeId: academicJournal
PreciseRelevancyScore: 0
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  Data: Aza-Wacker Cyclization Toward the Bridged Core of FR901483.
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  Data: <searchLink fieldCode="AR" term="%22Shen%2C+Defeng%22">Shen, Defeng</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Xie%2C+Changmin%22">Xie, Changmin</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Ruan%2C+Zhuwei%22">Ruan, Zhuwei</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Yang%2C+Chen%22">Yang, Chen</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Huang%2C+Sha-Hua%22">Huang, Sha-Hua</searchLink><relatesTo>2</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Zhu%2C+Lili%22">Zhu, Lili</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Hong%2C+Ran%22">Hong, Ran</searchLink><relatesTo>1</relatesTo> (AUTHOR)
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  Data: <searchLink fieldCode="JN" term="%22Synthesis%22">Synthesis</searchLink>. Jun2023, Vol. 55 Issue 12, p1940-1948. 9p.
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  Data: <searchLink fieldCode="DE" term="%22Double+bonds%22">Double bonds</searchLink><br /><searchLink fieldCode="DE" term="%22Tertiary+amines%22">Tertiary amines</searchLink><br /><searchLink fieldCode="DE" term="%22Ring+formation+%28Chemistry%29%22">Ring formation (Chemistry)</searchLink><br /><searchLink fieldCode="DE" term="%22Derivatization%22">Derivatization</searchLink><br /><searchLink fieldCode="DE" term="%22Amines%22">Amines</searchLink>
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: A nine-step synthetic route to access the tricyclic core of FR901483 is reported, featuring a key aza-Wacker cyclization step to construct an α-tertiary amine (ATA) in the bridged structure. The aza-Wacker protocol can tolerate both exocyclic and endocyclic double bonds, providing viable access to various bridged bicyclic rings bearing an ATA (e.g., 6-azabicyclo[3.2.1]octane, 7-azabicyclo[3.3.1]nonane, and 7-azabicyclo[4.2.1]nonane) in good to excellent yields. The synthetic studies presented herein enable structural derivatization of FR901483 to further exploit its compelling biological activities. [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
  Label:
  Group: Ab
  Data: <i>Copyright of Synthesis is the property of Georg Thieme Verlag Stuttgart 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.)
PLink https://search.ebscohost.com/login.aspx?direct=true&site=eds-live&db=egs&AN=163928318
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        Value: 10.1055/a-2012-5187
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      – Code: eng
        Text: English
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        PageCount: 9
        StartPage: 1940
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      – SubjectFull: Double bonds
        Type: general
      – SubjectFull: Tertiary amines
        Type: general
      – SubjectFull: Ring formation (Chemistry)
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            NameFull: Huang, Sha-Hua
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            NameFull: Zhu, Lili
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              M: 06
              Text: Jun2023
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              Y: 2023
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