70368-23-9Relevant academic research and scientific papers
Efficient enantioselective syntheses of sertraline, 2-epicatalponol and catalponol from tetralin-1,4-dione
Garcia, Alvaro Enriquez,Ouizem, Souad,Cheng, Xin,Romanens, Patrick,Kuendig, E. Peter
experimental part, p. 2306 - 2314 (2010/11/19)
Tetralin-1,4-dione, the stable tautomer of dihydroxynaphthalene, was reduced with catecholborane in the presence of 3,3-diphenyl-1-butyltetrahydro- 3H-pyrrolo[1,2-c][1,3,2]oxazaborole as catalyst to give enantiomerically highly enriched 4-hydroxy1-tetralone (99% ee) in an efficient one-pot procedure. The R-enantiomer provided a rapid access to sertraline while the S-enantiomer was converted into 2-epicatalponol and catalponol. A more selective enantioselective route to the antithermitic catalponol made use of the planar chiral tricarbonylchromium complex of hydroxytetralone. Its precursor chromium(tricarbonyl)[η6-(1-4,4a,8a)-tetralin-5,8dione] was obtained via direct complexation of 1,4-dihydroxynaphthalene using chromium(tricarbonyl)tris(ammonia) and boron trifluoride etherate as source of the chromium(tricarbonyl) fragment. Enolate prenylation was best carried out in the presence of a tetraamine ligand. Complete inversion of the stereogenic center bearing the prenyl group of the initially obtained tetralone complex was achieved via enolate formation followed by protonation.
Quinones and Related Compounds in Higher Plants. IX. Absolute Structures of Catalponol and Its Congeners
Inoue, Kenichiro,Inouye, Hiroyuki,Taga, Tooru,Fujita, Ryoji,Osaki, Kenji,et al.
, p. 1224 - 1229 (2007/10/02)
The absolute structure of (1a) of catalponol, a naphthoquinone congener of Catalpa ovata (Bignoniaceae), was revised to 1 on the basis of chemical correlation with isocatalponol (2), a substance of the same group occuring in Lippia origanoides (Verbenaceae).The validity of the absolute structure of 1 thus deduced, and hence those of isocatalponol (2) and catalponone (6), was verified by single crystal X-ray analysis of the p-bromobenzoate of 2-epicatalponol (9) derived from 1.Keywords-catalponol; isocatalponol; naphthoquinone congeners; absolute structure; X-ray analysis; CD spectra; Catalpa ovata; Bignoniaceae; Lippia origanoides; Verbenaceae.
