Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 11, Pages 2859-2863Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201713179
Keywords
carboacylation; C-C activation; reaction mechanisms; rhodium; total synthesis
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Funding
- NSFC [81502913, U1606403, U17062123]
- QNLMST [2015ASTP-ES14]
- 1000 Talents Plan for Young Professionals for a startup fund
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Described here is the first example of a rhodiumcatalyzed carboacylation/aromatization cascade of a C=O bond by C-C activation. In this transformation, a reactive rhodaindanone complex is regioselectively generated and adds across a C=O bond with subsequent elimination, thus providing a unique strategy to access a multisubstituted benzofuran scaffold. A diverse range of benzofuran analogues were obtained in good yields. Mechanistic studies show a tricyclic lactone was a viable intermediate. Application of this methodology to the total synthesis of C13-deOH-viniferifuran and C13-deOH-diptoindonesin G was achieved.
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