Submitted to: Synthetic Communications
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 6/11/2003
Publication Date: 6/17/2003
Citation: PETROSKI, R.J. OXIDATION OF MONOTETRAHYDROPYRANYLATED SHORT-CHAIN SYMMETRICAL DIOLS. SYNTHETIC COMMUNICATIONS. 2003. v. 33(18). p. 3243-3250.
Interpretive Summary: Due to customer concerns about the effect on the environment resulting from the continued use of broad-spectrum pesticides for crop protection and herbicides for the control of invasive weeds, we are developing pest and weed control strategies requiring the use of less pesticide and less herbicide. Insects produce a chemical substance, termed a pheromone, that selectively attracts members of its own species, usually for mating. We can use pheromone-baited traps in fields to monitor for the presence and numbers of specific insect pests and thus precisely time the use of pesticide sprays or measure the dispersal of a weed-biocontrol insect. There is strong interest in the use of certain insect pheromones as part of an effective strategy to control insect pests and invasive weeds; however, the pheromones are not available for use until robust synthetic pathways leading to the target compounds have been developed. Specifically, a new process has now been developed to prepare vital synthetic intermediates that should facilitate the production of certain insect pheromones for field evaluation. The potential use of these pheromones, in crop protection or invasive weed biocontrol, is more likely as a result of the research efforts.
Technical Abstract: The free hydroxyl functions of monotetrahydropyranylated three- to five-carbon symmetrical primary diols are oxidized to aldehydes, without cleavage of the protective group. By using a pyridinium dichromate in CH2Cl2, the oxidation procedure improved for these specific compounds. Anhydrous MgSO4 serves as a water scavenger.