88636-06-0

Upstream product

• 77877-20-4 (4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one 
• 123-38-6 propionaldehyde 
• 88636-04-8 (R)-2-Methyl-1-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-pentane-1,3-dione 

Downstream Products

• 88636-04-8 (R)-2-Methyl-1-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-pentane-1,3-dione 
• 176950-34-8 (4R,5S)-3-[(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-pentanoyl]-4-methyl-5-phenyl-oxazolidin-2-one 
• 149-31-5 (2S,3S)-2-methylpentane-1,3-diol 
• 86535-14-0 (2S,3S)-2-methyl-1-(4-methylbenzenesulfonyloxy)-3-pentanol 
• 155393-14-9 (2S,3S)-3-O-acetyl-2-methyl-1-O-p-toluenesulfonyl-1,3-pentanediol 

Relevant academic research and scientific papers

Asymmetric aldol condensation as a route to polypropionate derived pheromones

The synthesis of the polypropionate-derived pheromones sitophilate (1) and sitophilure (2) are described using an asymmetric aldol condensation as the key step to adduct 6; compound 6 was smoothly converted to the antipodes of each pheromone. This procedure can be expanded to more complicated structures with the same type of syn configuration such as stegobinone (3) and serricornin (4).

A short formal synthesis of (-)-serricornine

A short and efficient formal synthesis of serricornine (1), the sex pheromone of Lasioderma serricorne F., is described. The homochiral aldol 5 is straightforwardly converted to tosylate 9 to give homochiral lactone 2a (6 steps. 22% overall yield from oxazolidinone 4), a known precursor of (-)-1.