Expedient Route to the Functionalized Calyciphylline A-Type Skeleton via a Michael Addition–RCM Strategy

An efficient, robust, and scalable strategy to access the functionalized core of calyciphylline A-type alkaloids has been developed starting from commercially available 3-methylanisole. Key features of this approach are an intramolecular Michael addition/allylation sequence and a ring-closing metath...

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Bibliographic Details
Published in:Organic letters 2011-10, Vol.13 (19), p.5132-5135
Main Authors: Sladojevich, Filippo, Michaelides, Iacovos N, Darses, Benjamin, Ward, John W, Dixon, Darren J
Format: Article
Language:English
Subjects:
Anisoles - chemistry
Chemical Sciences
Models, Molecular
Molecular Structure
Polycyclic Compounds - chemical synthesis
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Summary:An efficient, robust, and scalable strategy to access the functionalized core of calyciphylline A-type alkaloids has been developed starting from commercially available 3-methylanisole. Key features of this approach are an intramolecular Michael addition/allylation sequence and a ring-closing metathesis step.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol202000w