218898-83-0Relevant academic research and scientific papers
A Biomimetic Approach to C-secolimonoids: Synthesis of CDE Ohchinolide and Nimbolidin Model Compounds
Mateos, A. Fernandez,Nava, E. Martin de la,Gonzalez, R. Rubio
, p. 1399 - 1402 (2001)
A concise and stereoselective synthesis of CDE ohchinolide and nimbolidin model compounds has been accomplished in ten and twelve steps respectively from α-cyclocitral, in 30 percent overall yield. The key step is a biomimetic type of allylic rearrangement induced by thionyl chloride. A potent insect antifeedant activity was found for two of the model compounds synthesised.
Synthesis of C-seco limonoid model insect antifeedants related to ohchinolide and nimbolidin
Fernandez-Mateos,Martin De La Nava,Rubio Gonzalez
, p. 1728 - 1734 (2007/10/03)
A concise and stereoselective synthesis of a CDE-seco limonoid related to ohchinolide and nimbolidin was accomplished in eleven and twelve steps, respectively, from α-cyclocitral. Opening of the C ring was first attempted by a retro-Claisen reaction, whereby a very unusual rearrangement occurred. However, the ring-opening was successfully accomplished by a selective Baeyer-Villiger reaction.
