Total Synthesis of (+)-Hyacinthacine A2 Based on SmI2-Induced Nitrone Umpolung.
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| Title: | Total Synthesis of (+)-Hyacinthacine A |
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| Authors: | Desvergnes, Stephanie1, Py, Sandrine1 sandrine.py@ujf-grenoble.fr, Vallée, Yannick1 |
| Source: | Journal of Organic Chemistry. 2/18/2005, Vol. 70 Issue 4, p1459-1462. 4p. 3 Diagrams. |
| Subjects: | Pyrrolizidines, Chemical bonds, Alkaloids, Cyclic compounds, Chemicals, Chemical reactions |
| Abstract: | A concise total synthesis of (+)-hyacinthacine A2, a polyhydroxylated pyrrolizidine alkaloid, is described using our recently discovered inversion of the C-N bond polarity in nitrones. In the key step, the diastereoselective reductive coupling of a L-xylose-derived cyclic nitrone with ethyl acrylate allowed the assembly of the bicyclic core of the target molecule, by way of a tandem formation of the C-C and C-N bonds. The method opens a novel, short, and general route for the synthesis of other pyrrolizidine alkaloids. [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 |
| FullText | Text: Availability: 0 |
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| Header | DbId: egs DbLabel: Engineering Source An: 16268601 AccessLevel: 6 PubType: Academic Journal PubTypeId: academicJournal PreciseRelevancyScore: 0 |
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| Items | – Name: Title Label: Title Group: Ti Data: Total Synthesis of (+)-Hyacinthacine A<subscript>2</subscript> Based on SmI<subscript>2</subscript>-Induced Nitrone Umpolung. – Name: Author Label: Authors Group: Au Data: <searchLink fieldCode="AR" term="%22Desvergnes%2C+Stephanie%22">Desvergnes, Stephanie</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Py%2C+Sandrine%22">Py, Sandrine</searchLink><relatesTo>1</relatesTo><i> sandrine.py@ujf-grenoble.fr</i><br /><searchLink fieldCode="AR" term="%22Vallée%2C+Yannick%22">Vallée, Yannick</searchLink><relatesTo>1</relatesTo> – Name: TitleSource Label: Source Group: Src Data: <searchLink fieldCode="JN" term="%22Journal+of+Organic+Chemistry%22">Journal of Organic Chemistry</searchLink>. 2/18/2005, Vol. 70 Issue 4, p1459-1462. 4p. 3 Diagrams. – Name: Subject Label: Subjects Group: Su Data: <searchLink fieldCode="DE" term="%22Pyrrolizidines%22">Pyrrolizidines</searchLink><br /><searchLink fieldCode="DE" term="%22Chemical+bonds%22">Chemical bonds</searchLink><br /><searchLink fieldCode="DE" term="%22Alkaloids%22">Alkaloids</searchLink><br /><searchLink fieldCode="DE" term="%22Cyclic+compounds%22">Cyclic compounds</searchLink><br /><searchLink fieldCode="DE" term="%22Chemicals%22">Chemicals</searchLink><br /><searchLink fieldCode="DE" term="%22Chemical+reactions%22">Chemical reactions</searchLink> – Name: Abstract Label: Abstract Group: Ab Data: A concise total synthesis of (+)-hyacinthacine A2, a polyhydroxylated pyrrolizidine alkaloid, is described using our recently discovered inversion of the C-N bond polarity in nitrones. In the key step, the diastereoselective reductive coupling of a L-xylose-derived cyclic nitrone with ethyl acrylate allowed the assembly of the bicyclic core of the target molecule, by way of a tandem formation of the C-C and C-N bonds. The method opens a novel, short, and general route for the synthesis of other pyrrolizidine alkaloids. [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: BibEntity: Identifiers: – Type: doi Value: 10.1021/jo048237r Languages: – Code: eng Text: English PhysicalDescription: Pagination: PageCount: 4 StartPage: 1459 Subjects: – SubjectFull: Pyrrolizidines Type: general – SubjectFull: Chemical bonds Type: general – SubjectFull: Alkaloids Type: general – SubjectFull: Cyclic compounds Type: general – SubjectFull: Chemicals Type: general – SubjectFull: Chemical reactions Type: general Titles: – TitleFull: Total Synthesis of (+)-Hyacinthacine A2 Based on SmI2-Induced Nitrone Umpolung. Type: main BibRelationships: HasContributorRelationships: – PersonEntity: Name: NameFull: Desvergnes, Stephanie – PersonEntity: Name: NameFull: Py, Sandrine – PersonEntity: Name: NameFull: Vallée, Yannick IsPartOfRelationships: – BibEntity: Dates: – D: 18 M: 02 Text: 2/18/2005 Type: published Y: 2005 Identifiers: – Type: issn-print Value: 00223263 Numbering: – Type: volume Value: 70 – Type: issue Value: 4 Titles: – TitleFull: Journal of Organic Chemistry Type: main |
| ResultId | 1 |
