Literature DB >> 24311180

Synthesis of stereoisomers of 8-methyl-2-decanol and esters attractive to severalDiabrotica sp.

P E Sonnet1, R L Carney, C Henrick.   

Abstract

Details of the syntheses of the four stereoisomers of 8-methyl-2-decanol and its propanoate ester are given. The racemic ester, two of its stereoisomers, and one stereoisomer as an acetate are attractive to several species ofDiabrotica. The key steps in the syntheses involve high-performance liquid chromatograpic resolutions of diastereomers to achieve high configurational enrichment of each site and generation of (R)-2-methylbutyric acid by chemical degradation ofD-isoleucine.

Entities:  

Year:  1985        PMID： 24311180     DOI： 10.1007/BF01012138

Source DB:  PubMed          Journal:  J Chem Ecol        ISSN： 0098-0331            Impact factor:   2.626


  4 in total

1.  Identification of a female-produced sex pheromone from the southern corn rootworm,Diabrotica undecimpunctata howardi Barber.

Authors:  P L Guss; J H Tumlinson; P E Sonnet; J R McLaughlin
Journal:  J Chem Ecol       Date:  1983-09       Impact factor: 2.626

2.  Identification of a female-produced sex pheromone of the western corn rootworm.

Authors:  P L Guss; J H Tumlinson; P E Sonnet; A T Proveaux
Journal:  J Chem Ecol       Date:  1982-02       Impact factor: 2.626

3.  Response ofDiabrotica virgifera virgifera, D. v. Zeae, andD. porracea to stereoisomers of 8-methyl-2-decyl propanoate.

Authors:  P L Guss; P E Sonnet; R L Carney; T F Branson; J H Tumlinson
Journal:  J Chem Ecol       Date:  1984-07       Impact factor: 2.626

4.  Response of northern corn rootworm,Diabrotica barberi Smith and Lawrence, to stereoisomers of 8-methyl-2-decyl propanoate.

Authors:  P L Guss; P E Sonnet; R L Carney; J H Tumlinson; P J Wilkin
Journal:  J Chem Ecol       Date:  1985-01       Impact factor: 2.626
  4 in total
  4 in total

1.  Preparation of 8-methyl-2-decanol: General synthesis of diastereomeric mixtures of alkyl branched insect pheromones.

Authors:  S R Abrams; A C Shaw
Journal:  J Chem Ecol       Date:  1987-08       Impact factor: 2.626

2.  Kinetic resolution of secondary alcohols with commercial lipases : Application to rootworm sex pheromone synthesis.

Authors:  P E Sonnet; M W Baillargeon
Journal:  J Chem Ecol       Date:  1987-05       Impact factor: 2.626

3.  Volatile organic compounds produced by the phytopathogenic bacterium Xanthomonas campestris pv. vesicatoria 85-10.

Authors:  Teresa Weise; Marco Kai; Anja Gummesson; Armin Troeger; Stephan von Reuß; Silvia Piepenborn; Francine Kosterka; Martin Sklorz; Ralf Zimmermann; Wittko Francke; Birgit Piechulla
Journal:  Beilstein J Org Chem       Date:  2012-04-17       Impact factor: 2.883

4.  Asymmetric Total Synthesis of Four Stereoisomers of the Sex Pheromone of the Western Corn Rootworm.

Authors:  Zhi-Feng Sun; Tao Zhang; Jinyang Liu; Zhen-Ting Du; Huaiji Zheng
Journal:  Molecules       Date:  2018-03-15       Impact factor: 4.411
  4 in total

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