29021-95-2Relevant academic research and scientific papers
OZONOLYSIS OF ALKENES AND REACTIONS OF POLYFUNCTIONAL COMPOUNDS. XXXII. SYNTHESIS OF (ξ)-3,7-DIMETHYL-2,7-OCTADIENYL PROPIONATE
Odinokov, V. N.,Kukovinets, O. S.,Zainullin, R. A.,Ishmuratov, G. Yu.,Isakova, L. A.,Tolstikov, G. A.
, p. 2017 - 2021 (2007/10/02)
3,7-Dimethyl-2,7-octadien-1-ol (with the E and Z isomers in a ratio of 85:15) was obtained by the ozonolysis of 1-methyl-1-cyclopentene and subsiquent selective transformation of the 1,1-dimethoxy-5-oxohexane, including ethoxycarbonylolefination and methylenation of the carbonyl groups and reduction of the ester group.The propionate of the product is a component of the sex pheromone of the San Jose scale insect.
Convenient Synthetic Route tp 6,8-Dioxabicyclooctanes, the Aggregation Pheromone Components of Bark Beetles
Joshi, Navalkishore N.,Mamdapur, Vasant R.,Chadha, Mohindra S.
, p. 2963 - 2966 (2007/10/02)
Convenient syntheses of (+/-)-frontalin (I) and (+/-)-brevicomins (IIa) and (IIb) were achieved from pent-4-en-1-ol (2) and pent-4-yn-1-ol (3).In a few simple and unambiguous steps, the alkenol (2) and the alkynol (3) were transformed into the acetal bromide (7) and the alkenyl bromides (14) and (17), respectively.Acylation of Grignard reagents of these bromides provided the corresponding methyl ketones (8), (15), and (18), the key intermediates for the synthesis of the title bicyclic acetals.The ketone (8) was converted into the olefin (9) which, on epoxidation followed by acid hydrolysis, yielded (+/-)-frontalin, whereas epoxidation of the alkenones (15) and (18) and subsequent cyclization afforded exo- and endo-brevicomin, stereoselectively.
