1612775-32-2Relevant academic research and scientific papers
Stereoselective Formation of Tetrahydrofuran Rings via [3 + 2] Annulation: Total Synthesis of Plakortone L
Sugimura, Hideyuki,Sato, Shougo,Tokudome, Kensei,Yamada, Takeshi
supporting information, p. 3384 - 3387 (2014/07/08)
The [3 + 2] annulation of 2,3-O-isopropylidene-aldehydo-aldose with methallyl ether leads to the stereoselective formation of a substituted tetrahydrofuran system, which is converted to a bicyclic lactone derivative via consecutive deprotection, oxidative cleavage of the terminal diol, oxidation of the resulting lactol, and Barton-McCombie deoxygenation. The efficiency of this process was demonstrated by the first total synthesis of Plakortone L.
