4117-09-3Relevant articles and documents
Concise syntheses of (7Z,11Z,13E)-hexadecatrienal and (8E,18Z)- tetradecadienal
Ma, Zengxiao,Yang, Xiaomei,Zhang, Yushun,Huang, Xiangzhong,Tao, Yunhai
scheme or table, p. 581 - 584 (2012/04/11)
Concise and efficient syntheses of (7Z,11Z,13E)-hexadecatrienal, a sex-pheromone component of the citrus leaf miner, and (8E,10Z)-tetradecadienal, the sex pheromone of the horse-chestnut leaf miner were described, starting from the commercially available acetylene and acrolein. The stereoselective formation of E,Z-conjugated double bond relied on cross-coupling between Grignard reagent and (E,Z)-bromodiene. The present syntheses achieved high overall yield (26% of the former and 23% for the latter) and high isomeric purity (97% for the former and 99% for the latter). Georg Thieme Verlag Stuttgart · New York.
Efficient synthesis of (S)-2-(cyclopentyloxycarbonyl)-amino-8-nonenoic acid: Key building block for BILN 2061, an HCV NS3 protease inhibitor
Wang, Xiao-Jun,Zhang, Li,Smith-Keenan, Lana L.,Houpis, Ioannis N.,Farina, Vittorio
, p. 60 - 63 (2012/12/26)
A new procedure for the practical synthesis of (S)-2-(cyclopen- tyloxycarbonyl)amino-8-nonenoic acid, a key building block for BILN 2061, an HCV NS3 protease inhibitor, has been developed. The key step features a kinetic resolution of racemic 2-acetylamino-8-nonenoic acid with acylase I. In addition, the undesired (R)-2-acetylamino-8-nonenoic acid was recycled after racemization. The procedure was implemented for the production of (S)-2-(cyclopentyloxycarbonyl)amino-8-nonenoic acid on pilot-plant scale.
Dilithium tetrachlorocuprate catalyzed coupling of allylmagnesium bromide with α,ω-dihaloalkanes
Johnson,Donohoe,Kang
, p. 1557 - 1564 (2007/10/02)
Allylmagnesium bromide has been shown to cross-couple with α,ω- dihaloalkanes in the presence of dilithium tetrachlorocuprate to yield, depending on reaction conditions, mono-coupled haloalkenes or di-coupled alkadienes. The order of the reactivity of the dihalides is I > Br >> CI and secondary halides show greater reactivity than primary halides.