1255151-62-2Relevant academic research and scientific papers
Construction of the ABC ring system of taxanes via stereoselective one-pot three-component coupling and intramolecular alkylation of a protected cyanohydrin ether
Serizawa, Takayuki,Miyamoto, Shigeru,Fuse, Shinichiro,Doi, Takayuki,Takahashi, Takashi
experimental part, p. 942 - 949 (2010/10/02)
Construction of the ABC ring system of taxanes via one-pot three-component coupling and intramolecular alkylation is accomplished. The 1,4-addition of a protected cyanohydrin ether to 2-methyl-2-cyclohexenone and subsequent addition of the resulting enolate to formaldehyde proceeded stereoselectively to provide the AC ring in 90% yield. The stereoselective reduction of the 2-keto group was achieved by using hydroxy-directed hydride reduction with LiAlH4. The intramolecular alkylation of the protected cyanohydrin ether furnished the ABC ring system of taxanes in 43% yield.
