Expedient Construction of the Vibsanin E Core without the Use of Protecting Groups

The tricyclic core of vibsanin E was constructed without the use of a protecting group in six steps. The El Gaïed Baylis−Hillman variant was key to allowing the Brønsted acid induced tandem cyclization forming rings B and C in one operation.

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Bibliographic Details
Published in:Organic letters 2005-03, Vol.7 (7), p.1327-1329
Main Authors: Heim, Ralf, Wiedemann, Stefan, Williams, Craig M, Bernhardt, Paul V
Format: Article
Language:English
Subjects:
Cyclization
Diterpenes - chemical synthesis
Diterpenes - chemistry
Molecular Structure
Viburnum - chemistry
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Description
Summary:The tricyclic core of vibsanin E was constructed without the use of a protecting group in six steps. The El Gaïed Baylis−Hillman variant was key to allowing the Brønsted acid induced tandem cyclization forming rings B and C in one operation.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0501222