1114822-26-2Relevant academic research and scientific papers
Asymmetric synthesis of iridoid derivatives using resolved 2-phenylindoline as a chiral auxiliary
Santangelo, Ellen M.,Liblikas, Ilme,Mudalige, Anoma,Toernroos, Karl W.,Norrby, Per-Ola,Unelius, C. Rikard
, p. 5915 - 5921 (2008)
An asymmetric synthetic route to cis,cis-nepetalactol (component of the sex pheromone for the hop aphid, Phorodon humuli) is presented. 2-Phenylindoline was resolved to provide a chiral auxiliary for the cycloaddition of oxocitral. The resolution was made by chromatographic separation of the diastereomers of the urea derivative made from 2-phenylindoline and with (R)-(+)-α- methylbenzyl isocyanate, followed by reductive cleavage of the isolated diasteromers using diborane. The cycloaddition of oxocitral using (S)-2-phenylindoline yielded an enantiopure product after chromatography. Hydrolysis of the cycloaddition adduct yielded gastrolactol (3). As gastrolactol is a versatile synthon for the synthesis of iridoids, the overall procedure provides a general asymmetric route to elaborated iridoids. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.
