119840-73-2Relevant academic research and scientific papers
Total synthesis of (+/-)-frondosin B and (+/-)-5-epi-liphagal by using a concise (4+3) cycloaddition approach
Laplace, Duchan R.,Verbraeken, Bart,Van Hecke, Kristof,Winne, Johan M.
, p. 253 - 262 (2014/01/17)
A recently developed (4+3) cycloaddition between dienes and furfuryl alcohols, as precursors of oxyallyl-type cations, has been used as a key step in the racemic syntheses of two natural products: frondosin B and liphagal. This work demonstrates the synthetic potential of this cycloaddition reaction, and offers a short synthetic route to an interesting family of natural products. A full account of these synthetic studies is presented, further illustrating the mechanism, scope, and limitations of this straightforward synthetic method for seven-membered rings. Cycloheptanes: Furfuryl alcohols serve as effective three-carbon dienophiles for a wide range of dienes in stereoselective cycloaddition reactions. This efficient reaction has been used to prepare two cycloheptanoid natural products, offering a conceptually straightforward and short synthetic entry into a biologically interesting class of polycyclic meroterpenoids (see scheme; TFA = trifluoroacetic acid). Copyright
Synthesis of all eight stereoisomers of the germination stimulant strigol
Reizelman,Scheren,Nefkens,Zwanenburg
, p. 1944 - 1951 (2007/10/03)
(+)-Strigol is a naturally occurring germination stimulant for the seeds of the parasitic weeds Striga and Orobanche. This paper describes the synthesis of all eight stereoisomers of strigol. The absolute configuration of these stereoisomers has been dedu
5-Demethylretinal and its 5-(2)H, 7-(2)H and 5,7-(2)H2 isotopomers. Synthesis, photochemistry and spectroscopy
Spijker-Assink, M. B.,Winkel, C.,Baldwin, G. S.,Lugtenburg, J.
, p. 125 - 131 (2007/10/02)
All-trans-5-demethylretinal and its 5-(2)H, 7-(2)H and 5,7-(2)H2 isotopomers have been synthesized by means of a new and simple scheme.Using photochemistry, the 9-, 11- and 13-cis, as well as the 9,13- and 11,13-di-cis-isomers, were obtained.The structure
