634153-27-8Relevant academic research and scientific papers
Use of a Sonogashira - Acetylide Coupling Strategy for the Synthesis of the Aromatic Spiroketal Skeleton of γ-Rubromycin
Tsang, Kit Y.,Brimble, Margaret A.,Bremner, John B.
, p. 4425 - 4427 (2003)
(Equation presented) The synthesis of the fused aromatic spiroketal core of γ-rubromycin is described via addition of an aryl acetylide fragment to an aryl acetaldehyde fragment. In turn, the aryl acetylene precursor was readily prepared with use of a Sonogashira reaction.
Bi(OTf)3-catalyzed tandem Meyer-Schuster rearrangement and 1,4-addition to the resulting vinyl ketone
Okamoto, Noriko,Sueda, Takuya,Yanada, Reiko
, p. 9854 - 9859 (2015/01/16)
Bi(OTf)3-catalyzed Meyer-Schuster rearrangement of electron-rich propargyl alcohols, followed by 1,4-addition of the resulting vinyl ketone, proceeded smoothly though Meyer-Schuster rearrangement of primary propargyl alcohols is rare. This tandem reaction can be extended to an intramolecular version, featuring a one-pot dihydroquinolone synthesis. (Chemical Equation Presented).
Synthesis of aromatic spiroacetals related to γ-rubromycin based on a 3H-spiro[1-benzofuran-2,2′-chromane] skeleton
Tsang, Kit Yee,Brimble, Margaret A.
, p. 6015 - 6034 (2008/02/02)
The synthesis of a series of aromatic 5,6-benzannelated and naphthyl-benzannelated spiroacetals related to the spiroacetal unit present in the quinonoid antibiotic γ-rubromycin is reported. The key steps include the use of Sonogashira coupling to construct an aryl acetylene that is coupled to an aryl aldehyde forming a propargyl alcohol intermediate. Hydrogenation of the resultant alkynol followed by oxidation produces a masked dihydroxyketone that upon treatment with silica-supported sodium hydrogen sulfate undergoes concomitant deprotection and cyclisation to afford the desired fused aromatic spiroacetal.
