- Stereocontrolled Synthesis of the Sex Pheromone of Nezara viridula (L.)
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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
- Baptistella, Lucia Helena Brito,Aleixo, Adriana Mendes
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p. 785 - 790
(2007/10/02)
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- 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
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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.
- Buss, Antony D.,Greeves, Nicholas,Mason, Ralph,Warren, Stuart
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p. 2569 - 2578
(2007/10/02)
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- The Stereocontrolled Horner-Wittig Reaction: Synthesis of Disubstituted Alkenes
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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.
- Buss, Antony D.,Warren, Stuart
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p. 2307 - 2326
(2007/10/02)
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- THE WITTIG-HORNER ROUTE TO TRI-SUBSTITUTED ALKENES: SYNTHESIS OF Z-α-BISABOLENE
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E and Z isomers of trisubstituted alkenes may separately be prepared by the Wittig-Horner reaction.Z-α-bisabolene has been made by this route.
- Buss, Antony D.,Warren, Stuart
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p. 111 - 114
(2007/10/02)
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