105329-29-1

Upstream product

• 90460-45-0 (4S,5E)-4-isopropyl-7-methylene-10-phenylthio-5-cyclodecen-1-one 
• 1212-08-4 S-Phenyl benzenethiosulfonate 
• 113589-95-0 methyl (2EZ,5R,8RS)-11-acetoxy-8-(2-methoxyethoxymethoxy)-5-(1-methylethyl)-2-phenylthio-2-undeceonate 
• 113589-99-4 Benzoic acid (E)-(S)-4-isopropyl-7-(2-methoxy-ethoxymethoxy)-1-phenylsulfanyl-cyclodec-2-enylmethyl ester 
• 113589-97-2 methyl (2EZ,5R,8RS)-8-(2-methoxyethoxymethoxy)-5-(1-methylethyl)-2-phenylthio-11-p-toluenesulfonyloxy-2-undeceonate 
• 113589-98-3 methyl (1RS,2E,4S,7RS)-7-(2-methoxyethoxymethoxy)-4-(1-methylethyl)-1-phenylthio-2-cyclodecene-1-ylcarboxylate 
• 113589-96-1 methyl (2EZ,5R,8RS)-11-hydroxy-8-(2-methoxyethoxymethoxy)-5-(1-methylethyl)-2-phenylthio-2-undeceonate 
• 113603-28-4 (1RS,2E,4S,7RS)-7-(2-methoxyethoxymethoxy)-4-(1-methylethyl)-1-phenylthio-2-cyclodecene-1-methanol 
• 113603-27-3 (3R,6RS)-9-acetoxy-6-(2-methoxyethoxymethoxy)-3-(1-methylethyl)-nonanal dimethylacetal 
• 113589-94-9 Acetic acid (R)-4-(2-methoxy-ethoxymethoxy)-8-methyl-7-(2-oxo-ethyl)-nonyl ester 
• 113590-02-6 (R)-7-(2,2-Dimethoxy-ethyl)-4-(2-methoxy-ethoxymethoxy)-8-methyl-nonanal 
• 112193-61-0 (R)-2-Allyl-6-(2,2-dimethoxy-ethyl)-7-methyl-3-oxo-octanoic acid methyl ester 
• 113589-93-8 (3R,6RS)-6-(2-methoxyethoxymethoxy)-3-(1-methylethyl)-9-decenal dimethylacetal 
• 113590-03-7 (R)-7-(2,2-Dimethoxy-ethyl)-4-(2-methoxy-ethoxymethoxy)-8-methyl-nonan-1-ol 

Downstream Products

• 61228-92-0 (3S,8R,9R,10S)-(-)-periplanone-B 

Relevant academic research and scientific papers

Method of manufacturing optically-active periplanone-b

Optically active periplanone-B is manufactured through oxidizing (1RS, 4S, 5E)-isopropyl-7-methylene-5-cyclodecene-1-ol. The oxidized product is regioselectively enolized and then sulfenylated. The sulfenylated product is oxidized and then subjected to decomposition of the sulfoxide. The decomposed product is epoxidated, and the epoxidated product is converted into an enolate which is then oxidized. The oxidized product is oxidized and then regio- and stereoselectively epoxidated to obtain optically active periplanone-B.

4-isopropyl-7-methylene-5-cyclodecen-1-ol

4-isopropyl-7-methylene-5-cyclodecen-1-ol is disclosed. The compound allows manufacture of optically active periplanone-B on an industrial scale.

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.