96481-69-5Relevant articles and documents
Enantioselective Synthesis of the Sex Pheromone of Lichen Moth, Miltochrista calamine, and Its Diastereomer
Yuan, Gucheng,Liu, Jiawei,Yu, Shihang,Wang, Xueyang,Bian, Qinghua,Wang, Min,Zhong, Jiangchun
, p. 80 - 83 (2021/10/05)
The synthesis of a Miltochrista calamine sex pheromone and its diastereomer has been developed. The key steps of the synthetic approach involved Evans' chiral auxiliaries and the addition of alkyne to aldehyde, which were firstly applied to prepare this sex pheromone and its diastereomer. The synthetic sex pheromone could be used to trap insects and study physiological and ecological questions of the lichen moth.
A New Asymmetric Synthesis of (S)-14-Methyloctadec-1-ene, the Sex Pheromone of the Peach Leafminer Moth
Bai, Hongjin,Du, Zhen-Ting,He, Guo-Guo,Liu, Lu,Tang, Meng,Wei, Liang,Zhang, Tao
, p. 1089 - 1095 (2020/07/25)
Abstract: An asymmetric synthesis of 14-methyl-1-octadecene, the sex pheromone of thepeach leafminer moth has been achieved. Based on the asymmetric methylation ofchiral (S)-4-benzyloxazolidin-2-one, thecarbon chain of the target molecule was assembled through aC1+C10+C4+C3procedure. The γ-lactone was transformed into 4-(benzyloxy)butanoic acid andthen, with the induction of Evan’s template, a chiral methyl group wasintroduced to the position of the carboxylic group in 97percent de. After reduction and a couple of chemicaloperations, the designed key intermediate A1was obtained. The synthesis of another moiety was started from decane-1,10-diolwhich was selectively protected and oxidized. The long carbon chain wasinstalled according to a Wittig protocol. After deprotection, oxidization, andmethylenation, the target molecule was synthesized in 7 linear steps with anoverall yield of 30.3percent.
Total Synthesis of Biselyngbyolide B
Sato, Eisuke,Tanabe, Yurika,Nakajima, Naoya,Ohkubo, Akifumi,Suenaga, Kiyotake
supporting information, p. 2047 - 2049 (2016/06/01)
The first total synthesis of biselyngbyolide B, an 18-membered macrolide, was achieved. The 18-membered ring structure was constructed by esterification using the Shiina reagent and an intramolecular Stille coupling reaction.