26059-43-8Relevant articles and documents
De Novo Asymmetric Synthesis of Phoracantholide J
Avocetien, Kenneth F.,Li, Jiazhen J.,Liu, Xiaofan,Wang, Yanping,Xing, Yalan,O'Doherty, George A.
, p. 4970 - 4973 (2016)
A de novo asymmetric total synthesis of the macrolide natural product (S)-phoracantholide J has been achieved in 10 steps from the commodity chemicals (1-pentyne, ethyl acrylate, acetaldehyde, and hydrogen). The asymmetry of the route was introduced by a Noyori reduction of a 3-yn-2-one, which makes the route equally amenable to the synthesis of either enantiomer. In addition, this route relies upon an alkyne zipper, a hydroalkynylation, and a macrolactonization to complete the synthesis.
Synthesis of the C7-C24 fragment of (-)-Macrolactin F
Oliveira, Roberta A.,Oliveira, Juliana M.,Rahmeier, Luis H.S.,Comasseto, Joao V.,Marino, Joseph P.,Menezes, Paulo H.
, p. 5759 - 5761 (2008)
An enantioselective and convergent synthesis of the C7-C24 fragment of Macrolactin F was achieved from four main fragments. A hydrotelluration/transmetalation sequence was used to install the E,Z diene present in the molecule, while a hydrozirconation/transmetalation sequence was used to connect two advanced intermediates.
Easy preparation of 1,4,5-trisubstituted 5-(2-alkoxy-1,2-dioxoethyl)-1,2,3- triazoles by chemoselective trapping of copper(I)-carbon bond with alkoxalyl chloride
Wang, Bo,Ahmed, Muhammad Naeem,Zhang, Jianlan,Chen, Wenwen,Wang, Xinyan,Hu, Yuefei
, p. 6097 - 6100 (2013/10/22)
We found that alkoxalyl chloride (ClCOCO2R) did not carry out an acylation on 1-copper(I) alkyne in solvent without additives, but chemoselectively on 5-copper(I) 1,2,3-triazole (an intermediate in cycloaddition of 1-copper(I) alkyne and azide). Thus, a one-pot preparation of 1,4,5-trisubstituted 5-(2-alkoxy-1,2-dioxoethyl)-1,2,3-triazole was achieved by simply stirring the mixture of 1-copper(I) alkyne, azide, and alkoxalyl chloride at room temperature for 4 h.
