Journal of the Chemical Society. Perkin transactions I p. 955 - 960 (1983)
Update date:2022-08-04
Topics:
Knight, David W.
Ojhara, Bol
A relatively short total synthesis of the true trail pheromone of Pharaoh's ant, (+/-)-faranal <(3SR,4RS)-(6E,10Z)-3,4,7,11-tetramethyltrideca-6,10-dienal (2)> is reported.The carbon skeleton was assembled by a Wittig condensation between (Z)-6-methyloct-5-en-2-one (4) and the 5-carboxypentylphosphonium salt (15).The ketone (4) was prepared in 'one-pot' and in a stereoselective manner using vinyl cuprate chemistry, while the relative stereochemistry of the two methyl substituents in the phosphonium salt (15) was established by using the Diels-Alder adduct (16) of buta-1,3-diene and maleic anhydride, which, after reduction and oxidative cleavage of the resulting cis-1,2-dimethylcyclohex-4-ene (18), gave only meso-3,4-dimethyladipic acid (19); this in turn was converted into the salt (15) in six straight-forward steps.
View MoreContact:+86-0512-88957371
Address:shanghai
Contact:86-371-63655023
Address:No.85,jinshui road,zhengzhou,China
SuZhou Hua-Emy Chemical Import and Export Co., LTD.
Contact:+86-512-88804994; +86-512-88804550;
Address:710, Building B, International Trade Center, 12 Huanghelu, Changshu, Jiangsu,China
Shanghai Yingrui Biopharma Co., Ltd
Contact:021-3358 8661*8003
Address:shanghai
Qingdao Pana-Life Biochem Co.,Ltd.
Contact:86-532-87683902
Address:No.967 Dalao Road, Licang Zone, Qingdao City,Shandong, China 266021
Doi:10.1007/BF03170450
(1939)Doi:10.1016/S0040-4039(01)92352-4
(1981)Doi:10.1021/jm00349a019
(1982)Doi:10.1002/ardp.19823150313
(1982)Doi:10.1021/jo00029a003
(1992)Doi:10.1055/s-1982-29763
(1982)
