73872-82-9

Upstream product

• 1826-67-1 vinyl magnesium bromide 
• 69083-80-3 4-bromo-5,5-dimethyl-2-cyclohexen-1-one 
• 82528-47-0 5-phenylseleno-2-ochtodene-1,6-diol 
• 4694-17-1 5,5-dimethlycyclohex-2-en-1-one 
• 82528-42-5 (EZ)-1-hydroxy-2-ochtoden-6-one 
• 82528-46-9 1-hydroxy-5-phenylseleno-2-ochtoden-6-one 
• 82528-38-9 1-acetoxy-6-phenylthio-2-ochtodene 
• 70473-42-6 [1-(1-Chloro-1-methyl-ethyl)-4-methylene-hex-5-enylsulfanyl]-benzene 
• 82528-43-6 Acetic acid 2-[5,5-dimethyl-cyclohex-3-en-(E)-ylidene]-ethyl ester 
• 123-35-3 7-methyl-3-methene-1,6-octadiene 
• 82528-45-8 5,6-epoxy-2-ochtoden-1-ol 
• 82528-41-4 (EZ)-6-oxo-2-ochtoden-1-yl trifluoroacetate 
• 82528-40-3 (EZ)-6-hydroxy-2-ochtoden-1-yl trifluoroacetate 
• 82528-37-8 1-chloro-6-phenylthio-2-ochtodene 

Downstream Products

• 73872-97-6 [5,5-Dimethyl-4-oxo-cyclohex-2-en-(Z)-ylidene]-acetaldehyde 
• 73872-95-4 Acetic acid (R)-4-[2-acetoxy-eth-(Z)-ylidene]-6,6-dimethyl-cyclohex-2-enyl ester 

Relevant academic research and scientific papers

SYNTHESES OF MARINE OCHTODANE ANTIFEEDANTS VIA HYDROLYTIC DEHALOGENATION

The syntheses of five naturally occurring antifeedants of the ochtodane ring system (1-ethyl-3,3-dimethylcyclohexane), previously isolated from the marine red alga Ochtodes crockeri, are reported.A key synthetic step involves the hydrolytic debromination of 6-bromo-1,4-ochtodien-3-ol.

SYNTHETIC STUDIES ON THE OCHTODANE TYPE TERPENES I. STEREOSELECTIVE CONSTRUCTION OF THE OCHTODANE SKELETON FROM MYRCENE.

The ochtodane skeleton, the Carbon framework of 1,1-dimethyl-3-ethylcyclohexane (1) was constructed highly stereoselectively by the acid-catalyzed (SnCl//4 or CF//3CO//2H) cyclization of the terminally functionalized myrcene derivatives, the benzenesulfenyl chloride adduct (7), the terminal beta -hydroxy sulfide (8) derived from 7, and myrcene 6,7-epoxide (10). The stereoselectivity of the 3-exo-double bond in 1 formed concomitantly in the cyclization reaction was found to depend remarkably upon the reaction temperture and the 85-94% of E-stereoselectivity was attained at minus 78 degree C. By the method, the ochtodane derivatives with the sulfur- or oxygen-functional groups on the C(6)-position were obtained.

NEW OCHTODANE SYNTHESES FROM MYRCENE

The ochtodane skeleton is formed stereoselectively from myrcene via acid-catalyzed cyclization of the benzenesulfenyl chloride adduct and the epoxide in a biogenetic type fashion.Its application to the syntheses of two ochtodane-type monoterpenes, an aldehyde component of the boll weevil pheromone and a diol found in the red alga Ochtodes crockeri, is reported.