Transannular Nitrone Cycloaddition. A Stereocontrolled Entry to the Spirocyclic Core of Pinnaic Acid

Thermolysis of lactone 18 initiated a stereospecific transannular nitrone−olefin [3 + 2] cycloaddition to yield tetracycle 19. Methanolysis followed by reductive cleavage of the isoxazolidine yielded 20, representing the azaspirocyclic core of pinnaic acid (1).

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Bibliographic Details
Published in:Organic letters 2001-02, Vol.3 (3), p.413-415
Main Authors: White, James D, Blakemore, Paul R, Korf, Eric A, Yokochi, Alexandre F. T
Format: Article
Language:English
Subjects:
Alkaloids - chemical synthesis
Crystallography, X-Ray
Nitrogen Oxides - chemistry
Spiro Compounds - chemical synthesis
Stereoisomerism
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Summary:Thermolysis of lactone 18 initiated a stereospecific transannular nitrone−olefin [3 + 2] cycloaddition to yield tetracycle 19. Methanolysis followed by reductive cleavage of the isoxazolidine yielded 20, representing the azaspirocyclic core of pinnaic acid (1).
ISSN:1523-7060
1523-7052
DOI:10.1021/ol000361j