First total synthesis of the sex pheromone of the oleander scale Aspidiotus nerii: An unusual sesquiterpenic functionalized cyclobutane

I Petschen, A Parrilla, MP Bosch, C Amela…

Index: Petschen, Ines; Parrilla, Alfredo; Bosch, M. Pilar; Amela, Cristina; Botar, Ana A.; Camps, Francisco; Guerrero, Angel Chemistry - A European Journal, 1999 , vol. 5, # 11 p. 3299 - 3309

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Citation Number: 21

Abstract

Abstract: The first total synthesis of the sex pheromone of the oleander scale Aspidiotus nerii (5), an economically important polyphagous pest, is described. The synthesis is based on a stereocontrolled and completely regioselective intramolecular exo-cyclization of cis- epoxynitrile 9 to afford cyclobutane alcohol t-10 stereoselectively. Introduction of the unusual 4-methylpent-4-enyl group onto the cyclobutane skeleton was effected through Wittig ...