165071-94-3Relevant academic research and scientific papers
SPIROPYRROLIDINE BETA-SECRETASE INHIBITORS FOR THE TREATMENT OF ALZHEIMER'S DISEASE
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Example 3.2, (2010/09/17)
The present invention is directed to spiropyrrolidine compounds of formula (I) which are inhibitors of the beta-secretase enzyme and that are useful in the treatment of diseases in which the beta-secretase enzyme is involved, such as Alzheimer's disease.
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.
A facile synthesis of fused aromatic spiroacetals based on the 3,4,3′,4′-tetrahydro-2,2′-spirobis(2H-1-benzopyran) skeleton
Brimble, Margaret A.,Flowers, Christopher L.,Trzoss, Michael,Tsang, Kit Y.
, p. 5883 - 5896 (2007/10/03)
The facile synthesis of a series of aromatic 6,6-spiroacetals based on the parent 3,4,3′,4′-tetrahydro-2,2′-spirobis(2H-1-benzopyran) heterocyclic system is reported. Key steps included the use of a Sonogashira coupling for the synthesis of an aryl acetylene that was coupled to an aryl aldehyde to form a propargyl alcohol intermediate. Hydrogenation of the alkynol followed by oxidation produced a masked dihydroxy ketone that upon treatment with trimethylsilyl bromide underwent deprotection and cyclisation to the 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.
A general synthesis of dihydrobenzofurans by intramolecular conjugate addition
Weeratunga, Gamini,Jaworska-Sobiesiak, Alina,Horne, Stephen,Rodrigo, Russel
, p. 2019 - 2023 (2007/10/02)
ortho Iodophenoxy crotonates 3e-7e cyclize to dihydrobenzofurans 1 and 9-12 when subjected to lithium-iodine exchange at -100 deg C.Naphtofuran 13 can be similarly obtained from α-iodonaphtoxy crotonate 8e.Methylation of this reaction mixture in
