483-66-9Relevant academic research and scientific papers
Ring-closing-metathesis-based synthesis of annellated coumarins from 8-allylcoumarins
Schultze, Christiane,Schmidt, Bernd
supporting information, p. 2991 - 2998 (2019/01/05)
8-Allylcoumarins are conveniently accessible through a microwave-promoted tandem Claisen rearrangement/Wittig olefination/ cyclization sequence. They serve as a versatile platform for the annellation of five- to seven-membered rings using ring-closing ole
A convenient synthesis of psoralens
Chimichi, Stefano,Boccalini, Marco,Cosimelli, Barbara,Viola, Giampietro,Vedaldi, Daniela,Dall'Acqua, Francesco
, p. 4859 - 4863 (2007/10/03)
An efficient synthesis (yields >70%) of linear 7H-furo[3,2-g]chromen-7-one derivatives (psoralens or furocoumarins) has been carried out starting from ring-substituted 2-(coumarin-7-yl)oxyaldehydes; moreover, the phototoxicity of these compounds has been tested on a cultured cell line of murine fibroblast.
Synthesis and antifungal activity of coumarins and angular furanocoumarins
Sardari, Soroush,Mori, Yoki,Horita, Kiyoshi,Micetich, Ronald G.,Nishibe, Sansei,Daneshtalab, Mohsen
, p. 1933 - 1940 (2007/10/03)
Angelicin, a naturally occurring furanocoumarin, that showed antifungal activity, was considered as a lead structure for a group of synthetic coumarins. Antifungal activities of the synthesized coumarins and angelicin derivatives were reported against Can
Two Regiocomplementary Approaches to Angular Furanocoumarins with Chromium Carbene Complexes: Synthesis of Sphondin, Thiosphondin, Heratomin, and Angelicin
Wulff, William D.,McCallum, J. Stuart,Kunng, Fen-Ann
, p. 7419 - 7434 (2007/10/02)
Two regiocomplementary syntheses of the angular furanocoumarin sphondin are described utilizing the benzannulation reaction of furylcarbene complexes of chromium.The high regioselectivity of an intermolecular synthesis employing the reaction of pentacarbonylchromium (8) and methyl 4-pentynoate is thought to be controlled by the preferred conformation of an alkyne-carbene complex intermediate.By utilizing the same acetylene, heratomin and an unnatural derivative of sphondin, 6-methoxy-2-oxo(2H)-thiofuro(2,3-h)benzopyran were prepared from pentacarbonylchromium (37) and pentacarbonylchromium (31), respectively.An intramolecular synthesis of sphondin from oxy>carbene>pentacarbonylchromium (10e) incorporates the acetylene with reversed regiochemistry due to the geometrical constraints of the intramolecular annulation.Control over the formation of the regiochemistry correct for the carbon skeleton of sphondin is possible due to the regioselectivity in the annulation of unsymmetrical aromatic substituents (3-furyl) on the carbene carbon.The intramolecular synthesis is thus related to the intermolecular synthesis by a double reversal in the regiochemistry.A convergent synthesis of sphondin and angelicin is described which has the phenol 72 produced from the intramolecular benzannulation of complex 10e as a branch point and is differentiated by whether the phenol functionality is retained or reduced.
