Russian Chemical Bulletin p. 98 - 99 (1993)
Update date:2022-08-03
Topics: Synthesis Enantiomer Chiral center Stereochemistry Enantioselective synthesis Optical rotation Chemical Synthesis Reaction Mechanism Chirality
Odinokov, V. N.
Ishmuratov, G. Yu.
Kharisov, R. Ya.
Serebryakov, E. P.
Tolstikov, G. A.
An optically active juvenile hormone analogue, S-(+)-methoprene (1), is synthesized in six steps from technical grade S-(+)-3,7-dimethyl-1,6-octadiene (''(+)-dihydromyrcene'', e.e. ca. 50percent) by a novel procedure which begins with selective hydroalumination-oxidation to give S-(-)-citronellol.This alcohol is oxidized to give S-(-)-citronellal which on reaction with allylmagnesium chloride affords 6S,10-dimethyl-1,9-undecadien-4R/S-ol (5).Smidt-Moiseev oxygenation of 5 followed by dehydration leads to 6S,10-dimethyl-3E,9-undecadien-2-one.The latter on treatment with isopropoxyethynylmagnesium bromide is transformed into isopropyl 3,7S,11-trimethyl-2E/Z,4E,10-dodecatrienoate which upon Brown solvomercuration-reduction in MeOH gives 1 in 14percent overall yield.
View MoreContact:86-379-63338609
Address:Jiudian Village,Deting Town,Song County,Luoyang
Synchem Pharma Co.,Ltd(expird)
Contact:+0086-21-61984905-1
Address:Building 60,Zimian Park, LongYang industrial Area, 1515Nong,Yuandong Road Fengxian District, Shanghai ,China
Contact:+31-24-3886056
Address:Binderskampweg 29 Unit 36
Shaanxi Lighte Optoelectronics Material Co., Ltd.
Contact:+86-29-88320728-622/619/620
Address:No.55 INDUSTRY ROAD 2,XI'AN NATIONAL CIVIL AEROSPACE INDUSTRIAL PARK.XI'AN China 710065.
Skyrun Industrial Co.,Ltd(expird)
website:http://www.chinaskyrun.com
Contact:0086-576-84610586
Address:Chemical Development Zone
Doi:10.1016/S0040-4039(97)10080-6
(1997)Doi:10.1081/SCC-120013716
(2002)Doi:10.1021/jm00333a047
(1964)Doi:10.1002/jps.2600810721
(1992)Doi:10.1002/jlac.199719971105
(1997)Doi:10.1016/S0968-0896(98)00080-7
(1998)