105897-89-0

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 105897-88-9 (E)-(R)-8,11-Dihydroxy-5-isopropyl-2-phenylsulfanyl-undec-2-enoic acid methyl ester 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 61228-92-0 (3S,8R,9R,10S)-(-)-periplanone-B 
• 105897-91-4 (1RS,2E,4S,7RS)-7-hydroxy-4-(1-methylethyl)-1-phenylthio-2-cyclodecene-1-methyl benzoate 
• 112193-69-8 [(E)-(S)-4-Isopropyl-1-phenylsulfanyl-7-(tetrahydro-pyran-2-yloxy)-cyclodec-2-enyl]-methanol 
• 105897-90-3 (E)-(S)-4-Isopropyl-1-phenylsulfanyl-7-(tetrahydro-pyran-2-yloxy)-cyclodec-2-enecarboxylic acid methyl ester 

Relevant academic research and scientific papers

TOTAL SYNTHESIS OF (-)-PERIPLANONE-B, THE SEX PHEROMONE OF THE AMERICAN COCKROACH

The total synthesis of (-)-periplanone-B, the sex excitant pheromone of the American cockroach, Periplaneta americana is accomplished starting from (+)-limonene.

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.