Publication details
Spirocyclisation of phytoalexin 1-methoxybrassinin in the presence of Grignard reagents
| Authors | |
|---|---|
| Year of publication | 2013 |
| Type | Article in Periodical |
| Magazine / Source | Chemical Papers |
| MU Faculty or unit | |
| Citation | |
| Doi | http://dx.doi.org/10.2478/s11696-013-0335-7 |
| Field | Organic chemistry |
| Keywords | phytoalexins; spirocyclisation; Grignard addition; spiroindolines; anti-proliferative activity |
| Description | The anti-cancer properties of naturally occurring (2R, 3R)-(-)-1-methoxyspirobrassinol methyl ether (I) and their synthetic amino or piperidyl analogues II inspired us to study the synthesis of new target compounds III with a C-C bond in the 2-position of indole rather than a C-N or C-O bond (I or II respectively). The goal was achieved via electrophilic-nucleophilic 3,2-difunctionalisation of 1-methoxybrassinin (IV ) in the presence of bromine and the Grignard reagent leading to the formation of cis- and trans-C-C analogues of I. Finally, the anti-cancer activities of the new compounds were measured and compared with I and II in order to show the importance of a heteroatom in the 2-substituted indole on the anti-cancer activity of spirobrassinols. |