Ahmad, S., Swift, M., Farrugia, L., Senn, H.M. and Sutherland, A. (2012) Stereoselective synthesis of functionalised carbocyclic amides: construction of the syn-(4aS,10bS)-phenanthridone skeleton. Organic and Biomolecular Chemistry, 10(19), pp. 3937-3945. (doi: 10.1039/C2OB25334H)
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Publisher's URL: http://dx.doi.org/10.1039/C2OB25334H
Abstract
A new synthetic approach has been developed for the preparation of 7-deoxypancratistatin analogues bearing a syn-(4aS,10bS)-phenanthridone ring junction. A one-pot tandem process involving a substratedirected Overman rearrangement and ring closing metathesis reaction was developed for the stereoselective synthesis of a carbocyclic allylic trichloroacetamide. Conversion to a 6-bromopiperonyl amide, followed by a Heck reaction generated a homoallylic alcohol and completed the syn-(4aS,10bS)- phenanthridone carbon skeleton. Stereoselective epoxidation and dihydroxylation of the syn-(4aS,10bS)- phenanthridone framework was then investigated leading to the preparation of new analogues of 7-deoxypancratistatin.
| Item Type: | Articles |
|---|---|
| Status: | Published |
| Refereed: | Yes |
| Glasgow Author(s) Enlighten ID: | Farrugia, Dr Louis and Swift, Mr Michael and Senn, Dr Hans and Ahmad, Mr Sajjad and Sutherland, Professor Andrew |
| Authors: | Ahmad, S., Swift, M., Farrugia, L., Senn, H.M., and Sutherland, A. |
| College/School: | College of Science and Engineering > School of Chemistry |
| Research Group: | WestCHEM |
| Journal Name: | Organic and Biomolecular Chemistry |
| ISSN: | 1477-0520 |
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