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Combined Metalation–Cross Coupling Strategies: A Synthesis of Schumanniophytine by a Key Biaryl O ‐Carbamate Remote Anionic Fries Rearrangement
Author(s) -
Macklin Todd K.,
Reed Mark A.,
Snieckus Victor
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200701116
Subject(s) - chemistry , metalation , fries rearrangement , carbamate , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , catalysis
Abstract A short synthesis of the alkaloid schumanniophytine ( 1 ) starting from simple building blocks and involving directed ortho metalation (D o M), 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)