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 |
|---|---|
| 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 |
