Asymmetric synthesis of the sex pheromone of the apple leafminer, Lyonetia prunifoliella
Authors:
- 27 December 2022
- Vol. 35 (2) , 118-128
Abstract
Lyonetia prunifoliella is a significant pest in orchards and damages apple. The sex pheromones of this pest were prepared via a new and concise method. The central to our method were Evans' chiral auxiliaries, the addition of chiral Grignard reagent to aldehyde and Wittig coupling.Keywords
This publication has 34 references indexed in Scilit:
- A practical synthesis of long-chain iso-fatty acids (iso-C12–C19) and related natural productsBeilstein Journal of Organic Chemistry, 2013
- A Convergent Synthesis of the C1−C16 Segment of Goniodomin A via Palladium-Catalyzed Organostannane−Thioester CouplingOrganic Letters, 2011
- (S,S)-(+)-Pseudoephedrine as Chiral Auxiliary in Asymmetric Conjugate Addition and Tandem Conjugate Addition/α-Alkylation ReactionsThe Journal of Organic Chemistry, 2006
- Catalytic asymmetric synthesis of enantiopure isoprenoid building blocks: application in the synthesis of apple leafminer pheromonesChemical Communications, 2005
- Total synthesis and biological evaluation of (+)-kalkitoxin, a cytotoxic metabolite of the cyanobacterium Lyngbya majusculaElectronic supplementary information (ESI) available: 1H NMR spectrum of synthetic (+)-kalkitoxin in C6D6. See http://www.rsc.org/suppdata/ob/b4/b404205k/Organic & Biomolecular Chemistry, 2004
- Synthesis and odour evaluation of stereoisomers of N‐Alkyl‐pyrrolidine derivatives, characteristic roast odour of seafoodFlavour and Fragrance Journal, 2003
- Fleming−Tamao Oxidation and Masked Hydroxyl Functionality: Total Synthesis of (+)-Pramanicin and Structural Elucidation of the Antifungal Natural Product (−)-PramanicinThe Journal of Organic Chemistry, 1999
- High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoidsJournal of the American Chemical Society, 1991
- Diastereoselective alkylation of 3-acylimidazolidin-2-ones: synthesis of (R)- and (S)-lavandulolThe Journal of Organic Chemistry, 1988
- Tertiary Phosphane/Tetrachloromethane, a Versatile Reagent for Chlorination, Dehydration, and P-N LinkageAngewandte Chemie International Edition, 1975