115693-97-5Relevant academic research and scientific papers
Stereocontrolled Synthesis of the Sex Pheromone of Nezara viridula (L.)
Baptistella, Lucia Helena Brito,Aleixo, Adriana Mendes
, p. 785 - 790 (2007/10/02)
The main component of the green stink bug Nezara viridula (L.) sex pheromone, the (Z)-(1S,2R,4S)-(-)-epoxybisabolene (1), has been synthesized by a convergent stereocontrolled sequence, using (S)-(-)-perillyl alcohol (2) as starting material. - Key Words: Pheromones / Green stink bug / Nezara viridula (L.) / Bisabolene, (Z)-(-)-epoxy / Epoxides
Applications of the Stereochemically-Controlled Horner-Wittig Reaction: Synthesis of Feniculin, (E)-Non-6-en-1-ol, a Pheromone of the Mediterranean Fruit Fly, (E)- and (Z)-Dec-5-en-1-ol, Tri-substituted Alkenes, and (Z)-α-Bisabolene
Buss, Antony D.,Greeves, Nicholas,Mason, Ralph,Warren, Stuart
, p. 2569 - 2578 (2007/10/02)
Stereoselective reduction of the appropriate α-diphenylphosphinoyl ketone or addition of the lithium derivative of an alkyl diphenylphospine oxide to an aldehyde or a ketone gives Horner-Wittig intermediates and hence the title compounds.
The Stereocontrolled Horner-Wittig Reaction: Synthesis of Disubstituted Alkenes
Buss, Antony D.,Warren, Stuart
, p. 2307 - 2326 (2007/10/02)
Addition of the lithium derivatives of phosphine oxides Ph2P(O)CH2R1 to aldehydes gives erythro adducts (11) with good stereoselectivity.Reduction of α-diphenylphosphinoyl ketones (12) gives threo adducts (11) with even better stereoselectivity.Purification by flash chromatography and/or crystallisation followed by elimination of Ph2PO2 gives pure Z- or E-alkenes with high material conversion.Explanations are offered for the stereoselectivities, conditions defined for full stereochemical control, and guidelines suggested for approaches to a given alkene.
