Spirocyclisation of phytoalexin 1-methoxybrassinin in the presence of Grignard reagents

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F13%3A00068413" target="_blank" >RIV/00216224:14310/13:00068413 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.2478/s11696-013-0335-7" target="_blank" >http://dx.doi.org/10.2478/s11696-013-0335-7</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.2478/s11696-013-0335-7" target="_blank" >10.2478/s11696-013-0335-7</a>

Result language
angličtina
Original language name
Spirocyclisation of phytoalexin 1-methoxybrassinin in the presence of Grignard reagents
Original language 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.
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Publication year
2013
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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