304434-23-9Relevant academic research and scientific papers
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.
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 (2007/10/03)
(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.
Studies in the total synthesis of heliquinomycinone: Proof of concept and assembly of a fully mature spirocyclization precursor
Qin, Donghui,Ren, Rex X.,Siu, Tony,Zheng, Changsheng,Danishefsky, Samuel J.
, p. 4709 - 4713 (2007/10/03)
A strategy for the synthesis of heliquinomycin, a selective helicase inhibitor, hinges on the spirocyclization of precursor 3. Naphthofuran 1 and aldehyde 2 were readily prepared and used in the synthesis of 3. The key steps in the total synthesis of heli
Synthesis of the bisbenzannelated spiroketal core of the γ-rubromycins. The use of a novel Nef-type reaction mediated by Pearlman's catalyst
Capecchi, Tanya,De Koning, Charles B.,Michael, Joseph P.
, p. 2681 - 2688 (2007/10/03)
The synthesis of the bisbenzannelated spiroketal core 6 of γ-rubromycin 1 from the substituted nitrostyrene 20 was achieved by using a novel Nef-type reaction mediated by Pearlman's catalyst. The precursor 28 was synthesised from readily prepared starting materials using Henry condensation chemistry. The product 6 was found to exist in two conformations in solution as shown by NMR spectroscopy.
