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Evaluation of 'east-to-west' ether-forming strategies for the total synthesis of maoecrystal V.

ABSTRACT: Model systems that evaluated different approaches to construct the central ether ring of maoecrystal V are described. Our first model systems attempted the ether formation using C-H functionalization reactions, which led to interesting rearrangements but none of the desired ether product. An intramolecular conjugate addition strategy was then explored that successfully formed the targeted C-O bond but resulted in the undesired stereochemistry.

SUBMITTER: Lazarski KE 

PROVIDER: S-EPMC3539776 | biostudies-literature | 2013 Feb

REPOSITORIES: biostudies-literature

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Evaluation of 'east-to-west' ether-forming strategies for the total synthesis of maoecrystal V.

Lazarski Kiel E KE   Akpinar Berkcan B   Thomson Regan J RJ  

Tetrahedron letters 20130201 7

Model systems that evaluated different approaches to construct the central ether ring of maoecrystal V are described. Our first model systems attempted the ether formation using C-H functionalization reactions, which led to interesting rearrangements but none of the desired ether product. An intramolecular conjugate addition strategy was then explored that successfully formed the targeted C-O bond but resulted in the undesired stereochemistry. ...[more]

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