Concise synthesis of (8Z,11Z,14Z)-8,11,14-heptadecatrienal, (7Z,10Z,13Z)-7,10,13-hexadecatrienal, and (8Z,11Z)-8,11-heptadecadienal, components of the essential oil of marine green alga Ulva pertusa.
The long-chain aldehydes, (8Z,11Z,14Z)-8,11,14-heptadecatrienal, (7Z,10Z,13Z)-7,10,13-hexadecatrienal, and (8Z,11Z)-8,11-heptadecadienal, were concisely synthesized by using Grignard coupling, catalytic hydrogenation with the Lindlar catalyst, and oxidation with Dess-Martin periodinane as the key steps. Particularly, (8Z,11Z,14Z)-8,11,14-heptadecatrienal and (7Z,10Z,13Z)-7,10,13-hexadecatrienal both possessed a seaweed-like odor.
Akakabe
Yoshihiko
Y
Department of Biological Chemistry, Faculty of Agriculture, Yamaguchi University, 1677-1 Yoshida, Yamaguchi 753-8515, Japan. akakabe@yamaguchi-u.ac.jp
Washizu
Kensuke
K
Matsui
Kenji
K
Kajiwara
Tadahiko
T
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D008956:Models, Chemical; D009812:Odorants; D009822:Oils, Volatile / Q000737:chemistry*; D044445:Ulva / Q000737:chemistry*
D000447:Aldehydes; D009822:Oils, Volatile