113589-95-0

Upstream product

• 105897-85-6 (R)-3-(1-methylethyl)-6-oxoheptanal dimethylacetal 
• 105897-86-7 (R)-3-(1-methylethyl)-6-oxo-9-decenal dimethylacetal 
• 113590-01-5 (R)-8-(2,2-Dimethoxy-ethyl)-9-methyl-dec-1-en-5-ol 
• 113590-03-7 (R)-7-(2,2-Dimethoxy-ethyl)-4-(2-methoxy-ethoxymethoxy)-8-methyl-nonan-1-ol 
• 113589-93-8 (3R,6RS)-6-(2-methoxyethoxymethoxy)-3-(1-methylethyl)-9-decenal dimethylacetal 
• 112193-61-0 (R)-2-Allyl-6-(2,2-dimethoxy-ethyl)-7-methyl-3-oxo-octanoic acid methyl ester 
• 113590-02-6 (R)-7-(2,2-Dimethoxy-ethyl)-4-(2-methoxy-ethoxymethoxy)-8-methyl-nonanal 
• 113589-94-9 Acetic acid (R)-4-(2-methoxy-ethoxymethoxy)-8-methyl-7-(2-oxo-ethyl)-nonyl ester 
• 113603-27-3 (3R,6RS)-9-acetoxy-6-(2-methoxyethoxymethoxy)-3-(1-methylethyl)-nonanal dimethylacetal 

Downstream Products

• 113589-96-1 methyl (2EZ,5R,8RS)-11-hydroxy-8-(2-methoxyethoxymethoxy)-5-(1-methylethyl)-2-phenylthio-2-undeceonate 
• 105897-91-4 (1RS,2E,4S,7RS)-7-hydroxy-4-(1-methylethyl)-1-phenylthio-2-cyclodecene-1-methyl benzoate 
• 105329-29-1 (4S,5E)-7-methylene-4-(1-methylethyl)-10-phenylsulfinyl-5-cyclodecene-1-one 
• 113589-98-3 methyl (1RS,2E,4S,7RS)-7-(2-methoxyethoxymethoxy)-4-(1-methylethyl)-1-phenylthio-2-cyclodecene-1-ylcarboxylate 
• 113589-97-2 methyl (2EZ,5R,8RS)-8-(2-methoxyethoxymethoxy)-5-(1-methylethyl)-2-phenylthio-11-p-toluenesulfonyloxy-2-undeceonate 
• 61228-92-0 (3S,8R,9R,10S)-(-)-periplanone-B 

Relevant academic research and scientific papers

TOTAL SYNTHESIS OF (-)-PERIPLANONE-B, NATURAL MAJOR SEX-EXCITANT PHEROMONE OF THE AMERICAN COCKROACH, PERIPLANETA AMERICANA

The total synthesis of (-)-periplanone-B 1, the major sex excitant and attractant pheromone of the American cockroach was accomplished starting from (+)-dihydrolimonene 2.Intramolecular alkylation of the substituted α-phenylthioacrylate 10 gave rise to the (E)-cyclodecene 11.Second key reaction was the reductive elimination of vicinal phenylthiobenzoate 14 to provide the cojugated diene 15.Overall yield of 1 through 28 steps was 0.5 percent.