Enantioselective synthesis and determination of the absolute configuration of the male sex pheromone of the parasitoid wasp Urolepis rufipes

Literature Information

Publication Date 2020-04-08
DOI 10.1039/D0OB00614A
Impact Factor 3.876
Authors

Kristina Melnik, Christopher Grimm, Johannes Wittbrodt, Joachim Ruther, Stefan Schulz


View Original

Abstract

Males of the parasitoid wasp Urolepis rufipes use 2,6-dimethyl-7-octene-1,6-diol as a sex pheromone to attract virgin females. Herein, we determine the absolute configuration of the pheromone to be (2S,6S)-2,6-dimethyl-7-octene-1,6-diol (2S,6S-6) and present a stereoselective synthesis of the natural enantiomer of this new linalool derivative. In addition, we show that female wasps respond to the natural 2S,6S-6 stereoisomer while 2R,6S-6 is behaviorally inactive.

Related Literature

Amorphous C/SbSx composites from natural stibnite as low cost and high performance lithium/sodium-ion battery anodes

Shuonan Wang, Kai Zhang, Hao Liu, Libing Liao

2023-10-26 Paper

DOI: 10.1039/D3TA05355E

NIR-activated quercetin-based nanogels embedded with CuS nanoclusters for the treatment of drug-resistant biofilms and accelerated chronic wound healing

Amit Nain, Yu-Ting Tseng, Akash Gupta, Yu-Feng Lin, Sangili Arumugam, Yu-Fen Huang

2023-09-19 Communication

DOI: 10.1039/D3NH00275F

The intrinsic activity descriptor of TM-N3-C single-atom catalysts for electrochemical CO2 reduction: a DFT study

Linmeng Wang, Zhiyuan Liu, Rushuo Li, Ping Yang, Wei Wang, Xiangdong Xue, Shihao Feng, Lingjing Yu, Ge Wang

2023-10-27 Paper

DOI: 10.1039/D3TA04806C

Defect engineering enhances plasmonic-hot electrons exploitation for CO2 reduction over polymeric catalysts

Zhehao Sun, Kaili Liu, Ary Anggara Wibowo, Julien Langley, Chao Zhang, Sandra E. Saji, Felipe Kremer, Dmitri Golberg, Hieu T. Nguyen, Nicholas Cox

2023-09-05 Communication

DOI: 10.1039/D3NH00348E

Electrifying H2O2 synthesis with g-C3N4-based single atom catalysts

Jungki Ryu

2023-10-04 Editorial

DOI: 10.1039/D3NH90041J

Coupling post-modification with reconstruction over Co-based metal–organic frameworks for electrochemical collective value-added recycling of nitrate and sulfion in wastewater

Tianlun Ren, Huizhen Wang, Shan Xu, Hongjie Yu, Kai Deng, Ziqiang Wang, Hongjing Wang, Liang Wang, You Xu

2023-10-24 Paper

DOI: 10.1039/D3TA04629J

Chemistry and bioactivity of lindenane sesquiterpenoids and their oligomers

Jun Luo, Danyang Zhang, Pengfei Tang, Nan Wang, Shuai Zhao, Lingyi Kong

2023-10-04 Review Article

DOI: 10.1039/D3NP00022B

Multistate switching of scanning tunnelling microscopy machined polyoxovanadate–dysprosium–phthalocyanine nanopatterns on graphite

Marco Moors, Irina Werner, Jens Bauer, Jonas Lorenz, Kirill Yu. Monakhov

2023-12-12 Communication

DOI: 10.1039/D3NH00345K

Ultrahigh-quality graphene resonators by liquid-based strain-engineering

Mario Hofmann, Chi-Te Liang, Ya-Ping Hsieh

2023-11-02 Communication

DOI: 10.1039/D3NH00420A

You might also like

Compound Q&A

What regulatory guidelines apply to 6-Bromo-2-methylimidazo[1,2-a]pyrimidine (CAS: 1111638-05-1)?

6-Bromo-2-methylimidazo[1,2-a]pyrimidine (CAS: 1111638-05-1) falls under various...

1111638-05-16-Bromo-2-methylimid...
Compound Q&A

Are there alternatives to 1-Pyrrolidineethanol, β-methyl-α-phenyl-, (αS,βR) (CAS: 123620-80-4) in synthesis?

While there are no direct alternatives, similar compounds like 1-Pyrrolidineetha...

123620-80-41-Pyrrolidineethanol...
Compound Q&A

Is 4-Methyl-2,6-bis(2-methyl-2-propanyl)phenyl methylcarbamate (CAS: 1918-11-2) safe?

4-Methyl-2,6-bis(2-methyl-2-propanyl)phenyl methylcarbamate (CAS: 1918-11-2) is ...

1918-11-24-Methyl-2,6-bis(2-m...
Compound Q&A

How should 2-(3-Bromo-4-fluorophenyl)-1,3-dioxolane (CAS: 77771-04-1) be stored?

2-(3-Bromo-4-fluorophenyl)-1,3-dioxolane (CAS: 77771-04-1) should be stored in a...

77771-04-12-(3-Bromo-4-fluorop...
Compound Q&A

What are the physical and chemical properties of 4,5,6,7-Tetrahydro-1H-indazole hydrochloride (CAS: 18161-11-0)?

4,5,6,7-Tetrahydro-1H-indazole hydrochloride is a white crystalline solid with a...

18161-11-04,5,6,7-Tetrahydro-1...
Compound Q&A

What is (2R)-1-Methoxy-3-phenyl-2-propanamine (CAS: 59919-07-2)?

(2R)-1-Methoxy-3-phenyl-2-propanamine is a chiral organic compound with the CAS ...

59919-07-2(2R)-1-Methoxy-3-phe...
Compound Q&A

What industries use Ethyl 1-(1-phenylethyl)-1H-imidazole-5-carboxylate (CAS: 56649-47-9)?

Ethyl 1-(1-phenylethyl)-1H-imidazole-5-carboxylate is used in various industries...

56649-47-9Ethyl 1-(1-phenyleth...
Compound Q&A

What regulatory guidelines apply to 4-[(1E,3S)-1-(4-Hydroxyphenyl)-1,4-pentadien-3-yl]phenol (CAS: 17676-24-3)?

4-[(1E,3S)-1-(4-Hydroxyphenyl)-1,4-pentadien-3-yl]phenol (CAS: 17676-24-3) falls...

17676-24-34-[(1E,3S)-1-(4-Hydr...
Compound Q&A

What industries use (S)-3-Amino-5-phenylpentanoic acid hydrochloride (CAS: 331846-97-0)?

(S)-3-Amino-5-phenylpentanoic acid hydrochloride is primarily used in the pharma...

331846-97-0(S)-3-Amino-5-phenyl...
Compound Q&A

How is 7-methoxy-1-benzothiophene-2-carboxylic acid (CAS: 88791-07-5) typically synthesized?

7-Methoxy-1-benzothiophene-2-carboxylic acid is typically synthesized by reactin...

88791-07-57-methoxy-1-benzothi...

Source Journal

Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
CiteScore: 3.4
Self-citation Rate: 10.3%
Articles per Year: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.