Combined Metalation-Cross Coupling Strategies: A Synthesis of Schumanniophytine by a Key Biaryl O-Carbamate Remote Anionic Fries Rearrangement

A short synthesis of the alkaloid schumanniophytine (1) starting from simple building blocks and involving directed ortho metalation (DoM), Suzuki–Miyaura cross coupling, and a key ortho‐silicon‐induced O‐carbamate remote anionic Fries rearrangement (3) is described. (© Wiley‐VCH Verlag GmbH & C...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2008-03, Vol.2008 (9), p.1507-1509
Main Authors: Macklin, Todd K., Reed, Mark A., Snieckus, Victor
Format: Article
Language:English
Subjects:
Total synthesis / Metalation / Directed remote metalation / C-C coupling
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Summary:A short synthesis of the alkaloid schumanniophytine (1) starting from simple building blocks and involving directed ortho metalation (DoM), Suzuki–Miyaura cross coupling, and a key ortho‐silicon‐induced O‐carbamate remote anionic Fries rearrangement (3) is described. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008) A short synthesis of the alkaloid schumanniophytine starting from simple building blocks and involving directed ortho metalation (DoM), Suzuki–Miyaura cross coupling, and a key ortho‐silicon‐directed remote anionic Fries rearrangement is described.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200701116