1430400-18-2Relevant articles and documents
Spirocyclisation of phytoalexin 1-methoxybrassinin in the presence of Grignard reagents
Ocenas, Peter,Tomasova, Lucia,Kutschy, Peter,Pazdera, Pavel,Mojzis, Jan,Pilatova, Martina
, p. 631 - 642 (2013)
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.