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Bidirectional Synthesis of 6-Acetoxy-5-hexadecanolide, the Mosquito Oviposition Pheromone of Culex quinquefasciatus, from a C-2-Symmetric Building Block Using Olefin Metathesis Reactions
- (5R,6S)-6-Acetoxy-5-hexadecanolide (MOP) is the oviposition pheromone of the mosquito Cx. quinquefasciatus, a vector of pathogens causing a variety of tropical diseases. We describe and evaluate herein three syntheses of MOP starting from mannitol-derived (3R,4R)-hexa-1,5-diene-3,4-diol. This C-2-symmetric building block is elaborated through bidirectional olefin metathesis reactions into 6-epi-MOP, which was converted into MOP via Mitsunobu inversion. The shortest of the three routes makes use of two sequential cross-metathesis reactions and an assisted tandem catalytic olefin reduction, induced by an in situ conversion of a Ru-carbene to a Ru-hydride.
Author details: | Bernd SchmidtORCiDGND, Monib H. Petersen, Diana Braun |
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DOI: | https://doi.org/10.1021/acs.joc.7b02944 |
ISSN: | 0022-3263 |
Pubmed ID: | https://pubmed.ncbi.nlm.nih.gov/29294276 |
Title of parent work (English): | The journal of organic chemistry |
Publisher: | American Chemical Society |
Place of publishing: | Washington |
Publication type: | Article |
Language: | English |
Date of first publication: | 2018/01/12 |
Publication year: | 2018 |
Release date: | 2022/01/26 |
Volume: | 83 |
Issue: | 3 |
Number of pages: | 7 |
First page: | 1627 |
Last Page: | 1633 |
Funding institution: | Deutsche Forschungsgemeinschaft (DFG)German Research Foundation (DFG) [Schm1095/6-2] |
Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
DDC classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
Peer review: | Referiert |