86797-90-2

Upstream product

• 115557-14-7 (1'S,2'R)-1'-ethyl-2'-methyl-3'-oxopentyl (2S,3S)-3-[(tert-butyl)dimethylsilyloxy]-2-methylpentanoate 
• 211621-52-2 1'-ethylpropyl 3-hydroxy-2-methylpentanoate 
• 122798-53-2 (2S,3S) 1'-ethylpropyl 3-hydroxy-2-methylpentanoate 
• 207788-53-2 3,5-Dinitro-benzoic acid (1S,2S)-1-ethyl-2-(1-ethyl-propoxycarbonyl)-propyl ester 
• 108779-16-4 (2S,3S)-3-tert-butyldimethylsilyloxy-2-methylpentanoic acid 
• 122744-57-4 1-ethylpropyl 3S-tert-butyldimethylsilyloxy-2S-methylpentanoate 
• 133444-39-0 N-{(2S,3S)-3-[(tert-butyl)dimethylsilyloxy]-2-methylpentanoyl}bornane-10,2-sultam 
• 133444-40-3 N-((2S,3S)-3-hydroxy-2-methylpentanoyl)bornane-10,2-sultam 

Relevant academic research and scientific papers

An Efficient Enantioselective Synthesis of (-)-Serricorole

The cigarette beetle pheromone (-)-serricorole (1) has been synthesized in 23percent overall yield by an eight-step sequence starting from N-propionylsultam 3.The synthesis features asymmetric anti- and syn-aldolizations 3 -> 4 and 8 -> 9, a non-destructi

A flexible stereocontrolled synthesis of β-hydroxy-α-methyl esters: Application to the synthesis of stegobiol and serricorole

β-Hydroxy-α-methyl esters have been obtained in a stereocontrolled manner and high enantiomeric and diastereomeric purity from commercially available methyl 3-oxopentanoate and methyl 3-oxobutanoate. The key step is file catalytic hydrogenation of the carbonyl group using (R)- or (S)-BINAP- Ru as chiral catalyst followed by asymmetric alkylation. Stegobiol and serricorole, components of the sex pheromone of the drugstore beetle, Stegobium paniceum (L.) and cigarette beetle, Lasioderma serricorne (F.), have been prepared from these chiral building blocks without the need for stoichiometric amounts of chiral auxiliaries.

Synthesis and Absolute Configuration of Serricorole and Serricorone, Sex Pheromone Components of Cigarette Beetle

(2S,3R,1'S,2'S)-Serricorole (1) and (2S,3R,1'R)-serricorone (2), sex pheromone components of the cigarette beetle (Lasioderma serricorne F.), were synthesized, starting from the enantiomers of methyl 3-hydroxypentanoate.The stereochemistry of the naturally 1 was determined to be 2S,3R,1'S,2'S, and that of 2 to be 2S,3R,1'RS by comparing between the CD spectra of the natural and synthetic samples.