Calder, E. D.D., McGonagle, F. I., Harkiss, A. H., McGonagle, G. A. and Sutherland, A. (2014) Preparation of amino-substituted indenes and 1,4-dihydronaphthalenes using a one-pot multireaction approach: total synthesis of oxybenzo[c]phenanthridine alkaloids. Journal of Organic Chemistry, 79(16), pp. 7633-7648. (doi: 10.1021/jo5014492) (PMID:25060853)
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Abstract
Allylic trichloroacetimidates bearing a 2-vinyl or 2-allylaryl group have been designed as substrates for a one-pot, two-step multi-bond-forming process leading to the general preparation of aminoindenes and amino-substituted 1,4-dihydronaphthalenes. The synthetic utility of the privileged structures formed from this one-pot process was demonstrated with the total synthesis of four oxybenzo[c]phenanthridine alkaloids, oxychelerythrine, oxysanguinarine, oxynitidine, and oxyavicine. An intramolecular biaryl Heck coupling reaction, catalyzed using the Hermann–Beller palladacycle was used to effect the key step during the synthesis of the natural products.
| Item Type: | Articles |
|---|---|
| Status: | Published |
| Refereed: | Yes |
| Glasgow Author(s) Enlighten ID: | Calder, Mr Ewen and Harkiss, Dr Alexander and McGonagle, Miss Fiona and Sutherland, Professor Andrew |
| Authors: | Calder, E. D.D., McGonagle, F. I., Harkiss, A. H., McGonagle, G. A., and Sutherland, A. |
| College/School: | College of Science and Engineering > School of Chemistry |
| Journal Name: | Journal of Organic Chemistry |
| Publisher: | American Chemical Society |
| ISSN: | 0022-3263 |
| ISSN (Online): | 1520-6904 |
| Copyright Holders: | Copyright © 2014 American Chemical Society |
| First Published: | First published in Journal of Organic Chemistry 79(16):7633-7648 |
| Publisher Policy: | Reproduced under a Creative Commons License |
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