trans-Acetonide Controlled endo-Selective Intramolecular Nitrone−Alkene Cycloaddition of Hept-6-enoses:  A Facile Entry to Calystegines, Tropanes, and Hydroxylated Aminocycloheptanes

High-yielding endo-selective intramolecular nitrone−alkene cycloaddition (INAC) reactions of hept-6-enoses controlled by a trans-acetonide to give bridged bicyclo[4.2.1]isoxazolidines exclusively are realized for the first time. The cycloadducts were readily transformed into calystegine, tropane, an...

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Bibliographic Details
Published in:Organic letters 2007-01, Vol.9 (2), p.207-209
Main Authors: Shing, Tony K. M, Wong, Wai F, Ikeno, Taketo, Yamada, Tohru
Format: Article
Language:English
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Summary:High-yielding endo-selective intramolecular nitrone−alkene cycloaddition (INAC) reactions of hept-6-enoses controlled by a trans-acetonide to give bridged bicyclo[4.2.1]isoxazolidines exclusively are realized for the first time. The cycloadducts were readily transformed into calystegine, tropane, and hydroxylated aminocycloheptane frameworks.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol062621o