169137-67-1Relevant articles and documents
Phosphine/palladium-catalyzed syntheses of alkylidene phthalans, 3-deoxyisoochracinic acid, isoochracinic acid, and isoochracinol
Fan, Yi Chiao,Kwon, Ohyun
supporting information; experimental part, p. 3264 - 3267 (2012/08/28)
In this study we used sequential catalysis-PPh3-catalyzed nucleophilic addition followed by Pd(0)-catalyzed Heck cyclization-to construct complex functionalized alkylidene phthalans rapidly, in high yields, and with good stereoselectivities (E/Z ratios of up to 1:22). The scope of this Michael-Heck reaction includes substrates bearing various substituents around the alkylidene phthalan backbone. Applying this efficient sequential catalysis, we accomplished concise total syntheses of 3-deoxyisoochacinic acid, isoochracinic acid, and isoochracinol.
A facile and regioselective synthesis of donor-substituted 2-(2-halophenyl)acetaldehyde acetals
Wunsch,Nerdinger
, p. 301 - 305 (2007/10/02)
Starting from vanillin (5a) a facile and high yielding procedure for the preparation of the donor substituted (2-bromophenyl)- and (2-iodophenyl)-acetaldehyde acetals 13c and 16c is described. Homologization of O-benzylvanillin to obtain the phenylacetaldehyde acetal 15c succeeds by Wittig reaction with the phosphonium chloride 11 and subsequent addition of methanol. 15c is brominated with pyridinium bromide perbromide in methanol to yield the bromo acetal 13c in 65% yield from vanillin. Iodination of 15c with iodine and iodic acid leads to the iodo acetal 16c.
