475168-00-4Relevant academic research and scientific papers
Practical access to spiroacetal enol ethers via nucleophilic dearomatization of 2-furylmethylenepalladium halides generated by Pd-catalyzed coupling of furfural tosylhydrazones with aryl halides
Yin, Biaolin,Zhang, Xiaoyu,Liu, Jianchao,Li, Xuehui,Jiang, Huanfeng
, p. 8113 - 8116 (2014/07/21)
Pd-catalyzed cross-coupling of furfural tosylhydrazones with aryl halides produces 2-furylmethylenepalladium halides, which can undergo intramolecular nucleophilic dearomatization to provide spiroacetal enol ethers. This is the first report on the formati
Rapid and stereoselective synthesis of spirocyclic ethers via the intramolecular Piancatelli rearrangement
Palmer, Leoni I.,De Alaniz, Javier Read
supporting information, p. 476 - 479 (2013/04/10)
The first example of a Piancatelli rearrangement of alcohols is demonstrated utilizing dysprosium(III) triflate as a catalyst to access oxaspirocycles in a highly diastereoselective manner. The cascade reaction constructs the spirocyclic ether ring system and the tertiary stereocenter in a single operation and is experimentally easy to perform.
A straightforward synthetic approach to the spiroketal-enol ethers synthesis of natural antifeeding compound tonghaosu and its analogs
Gao, Yang,Wu, Wen-Lian,Wu, Yu-Lin,Ye, Bin,Zhou, Rong
, p. 12523 - 12538 (2007/10/03)
Tonghaosu 1, a natural product discovered from several plants of tribe Athemdeae, is a [4.4]spiroketal with an enediyne side-chain and shows interesting insect antifeeding activity. In this paper a general and convenient synthetic methodology for the synthesis of 1, 2 and its spiroketal-enol ether derivatives is described. Thus, 3-(2'-furyl)-propan-1- ol 7a or 4-(2'-furyl)-butan-1-ol 7b prepared from furaldehyde was treated with n-butyl lithium and unsaturated aldehyde to provide the diol 5. Diol 5 could also be obtained from 5-(3-acetoxypropyl)-2-furaldehyde or 5-(4- acetoxybutyl)-2-furaldehyde and alkynyllithium. By careful treatment of 5 or 7 with acid, dehydration-cyclization occurred to give the desired spiroketal- enol ether in moderate to excellent yields.
