Synthesis of Tenuifolin via Intramolecular Nicholas Reaction

Authors

Sinisa Djurdjevic, University of WindsorFollow
James R. Green, University of WindsorFollow

Document Type

Article

Publication Date

10-2014

Publication Title

Synlett

Volume

25

Issue

17

First Page

2467

Keywords

alkynes, total synthesis, carbocation, fused-ring systems, electrophilic aromatic substitution, transition metals

Last Page

2470

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.

DOI

10.1055/s-0034-1379009 letter

Funding Reference Number

NSERC

Comments

First published in Synlett, copyright © Georg Thieme Verlag, an imprint of Thieme Publishing. To access the final version, see DOI: 10.1055/s-0034-1379009 at https://www.thieme-connect.com/products/ejournals/html/10.1055/s-0034-1379009

Recommended Citation

Djurdjevic, Sinisa and Green, James R.. (2014). Synthesis of Tenuifolin via Intramolecular Nicholas Reaction. Synlett, 25 (17), 2467-2470.
https://scholar.uwindsor.ca/chemistrybiochemistrypub/68