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Synlett 2014; 25(17): 2467-2470
DOI: 10.1055/s-0034-1379009
DOI: 10.1055/s-0034-1379009
letter
Synthesis of Tenuifolin through Intramolecular Nicholas Reaction
Further Information
Publication History
Received: 30 June 2014
Accepted after revision: 30 July 2014
Publication Date:
08 September 2014 (online)
Abstract
The synthesis of the Cinnamomum homosesquiterpenoid tenuifolin has been accomplished by way of an intramolecular Nicholas reaction of the [Co2(CO)6] complex of an alkyne-substituted biaryl for construction of the seven-membered ring. The cyclization features the reaction of a nonactivated arene ring with the propargyldicobalt cation to give the dibenzocycloheptyne-Co2(CO)6.
Key words
alkynes - total synthesis - carbocation - fused-ring systems - electrophilic aromatic substitution - transition metalsSupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083.
- Supporting Information
-
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For recent Nicholas reaction reviews, see:
For the original Nicholas publications, see: