82528-46-9

Upstream product

• 1666-13-3 diphenyl diselenide 
• 82528-42-5 (EZ)-1-hydroxy-2-ochtoden-6-one 
• 82528-41-4 (EZ)-6-oxo-2-ochtoden-1-yl trifluoroacetate 
• 82528-40-3 (EZ)-6-hydroxy-2-ochtoden-1-yl trifluoroacetate 

Downstream Products

• 73872-82-9 2,4-ochtodien-1,6-diol 
• 73872-82-9 (+/-)-(2Z)-2,4-ochtodadiene-1,6-diol 
• 82528-47-0 5-phenylseleno-2-ochtodene-1,6-diol 

Relevant academic research and scientific papers

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.