Syntheab of racemic lineatin (l), a pheromone component of Trypodendron lineatum, is described. Condensation of 5methyl-5hexen-2-one (2) and triethyl phosphonoacetate with Lfl (SiMe& gave eaters 3, which upon hydrolysis gave acids 4a-f. The bicyclo [3.2. 0] ring compounds 5 and 6 were obtained via an intramolecular [2+ 2) addition by refluxing underivatized carboxylic acids 4a-f with NaOAc and AczO. Compound 5 was isomerized ...
[Ishiyama, Jun-ichi; Maeda, Satoshi; Takahashi, Kazuhiro; Senda, Yasuhisa; Imaizumi, Shin Bulletin of the Chemical Society of Japan, 1987 , vol. 60, # 5 p. 1721 - 1726]