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An Efficient Enantioselective Synthesis of (2R)-Hydroxymethyl Glutamic Acid and an Approach to the (2R)-Hydroxymethyl-Substituted Sphingofungins.

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Title: An Efficient Enantioselective Synthesis of (2R)-Hydroxymethyl Glutamic Acid and an Approach to the (2R)-Hydroxymethyl-Substituted Sphingofungins.
Authors: Hayes, Christopher J.1 chris.hayes@nottingham.ac.uk, Bradley, Daniel M.1, Thomson, Nicholas M.2
Source: Journal of Organic Chemistry. 3/31/2006, Vol. 71 Issue 7, p2661-2665. 5p. 4 Diagrams.
Subjects: Enantioselective catalysis, Methanol, Glutamic acid, Aldehydes, Carbenes, Natural products, Organic chemistry
Abstract: We have developed a short enantioselective synthesis of (2R)-hydroxymethyl glutamic acid (HMG) starting from Garner's aldehyde using an alkylidene carbene 1,5-CH insertion as a method to construct the quaternary stereocenter. A variety of conditions were examined for the oxidative cleavage of the key cyclopentene intermediate and we found that RuC13/NalO4 led directly to the desired amino bis-acid product. We were also able to show that oxidative cleavage of the cyclopentene 1,5-CH insertion product could be used to produce the amino acid-containing skeleton of the sphingofungin family of natural products. [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.)
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An: 20531302
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PubTypeId: academicJournal
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  Data: <searchLink fieldCode="AR" term="%22Hayes%2C+Christopher+J%2E%22">Hayes, Christopher J.</searchLink><relatesTo>1</relatesTo><i> chris.hayes@nottingham.ac.uk</i><br /><searchLink fieldCode="AR" term="%22Bradley%2C+Daniel+M%2E%22">Bradley, Daniel M.</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Thomson%2C+Nicholas+M%2E%22">Thomson, Nicholas M.</searchLink><relatesTo>2</relatesTo>
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  Data: <searchLink fieldCode="JN" term="%22Journal+of+Organic+Chemistry%22">Journal of Organic Chemistry</searchLink>. 3/31/2006, Vol. 71 Issue 7, p2661-2665. 5p. 4 Diagrams.
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  Data: <searchLink fieldCode="DE" term="%22Enantioselective+catalysis%22">Enantioselective catalysis</searchLink><br /><searchLink fieldCode="DE" term="%22Methanol%22">Methanol</searchLink><br /><searchLink fieldCode="DE" term="%22Glutamic+acid%22">Glutamic acid</searchLink><br /><searchLink fieldCode="DE" term="%22Aldehydes%22">Aldehydes</searchLink><br /><searchLink fieldCode="DE" term="%22Carbenes%22">Carbenes</searchLink><br /><searchLink fieldCode="DE" term="%22Natural+products%22">Natural products</searchLink><br /><searchLink fieldCode="DE" term="%22Organic+chemistry%22">Organic chemistry</searchLink>
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  Data: We have developed a short enantioselective synthesis of (2R)-hydroxymethyl glutamic acid (HMG) starting from Garner's aldehyde using an alkylidene carbene 1,5-CH insertion as a method to construct the quaternary stereocenter. A variety of conditions were examined for the oxidative cleavage of the key cyclopentene intermediate and we found that RuC13/NalO4 led directly to the desired amino bis-acid product. We were also able to show that oxidative cleavage of the cyclopentene 1,5-CH insertion product could be used to produce the amino acid-containing skeleton of the sphingofungin family of natural products. [ABSTRACT FROM AUTHOR]
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  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/jo052408q
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      – Code: eng
        Text: English
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        PageCount: 5
        StartPage: 2661
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      – SubjectFull: Enantioselective catalysis
        Type: general
      – SubjectFull: Methanol
        Type: general
      – SubjectFull: Glutamic acid
        Type: general
      – SubjectFull: Aldehydes
        Type: general
      – SubjectFull: Carbenes
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      – SubjectFull: Natural products
        Type: general
      – SubjectFull: Organic chemistry
        Type: general
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      – TitleFull: An Efficient Enantioselective Synthesis of (2R)-Hydroxymethyl Glutamic Acid and an Approach to the (2R)-Hydroxymethyl-Substituted Sphingofungins.
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            NameFull: Hayes, Christopher J.
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            NameFull: Bradley, Daniel M.
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            NameFull: Thomson, Nicholas M.
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            – D: 31
              M: 03
              Text: 3/31/2006
              Type: published
              Y: 2006
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