66820-34-6Relevant academic research and scientific papers
Catalytic Dehydrative Lactonization of Allylic Alcohols
Liu, Ji,Miotto, Romain J.,Segard, Julien,Erb, Ashley M.,Aponick, Aaron
, p. 3034 - 3038 (2018/05/28)
A convenient strategy for the synthesis of phthalides and ?-butyrolactones is reported. The method utilizes readily prepared allylic alcohols in formal Au(I)- and Pd(II)-catalyzed SN2′ reactions. Using these catalysts, exclusive formation of the desired five-membered lactones is observed, completely avoiding the competing direct lactonization pathway that forms the undesired seven-membered ring with protic acids and alternative metal salts. This mild and operationally simple method notably tolerates exomethylene groups and should find use in both phthalide and terpene syntheses.
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.
Directed ortho metalation of n,n-diethyl benzamides. Methodology and regiospecific synthesis of useful contiguously tri- and tetra-substituted oxygenated aromatics, phthalides and phthalic anhydrides
De Silva,Reed,Billedeau,Wang,Norris,Snieckus
, p. 4863 - 4878 (2007/10/02)
Full experimental details for the directed ortho metalation approch to a variety of simple ortho-substituted N,N-diethyl benzamides (Table 1) and contiguously 1,2,3- and 1,2,3,4-substituted benzamides (Tables 2) are given. The efficient conversion of these benzamides (6, 10, 12, 13, 18, 19) into phthalides (9a-b, 16b-c, 17) and phthalic anhydrides (8,16a), compounds previously available by demanding, classical methods, is detailed. A short synthesis of iso-ochracinic acid (27) is described.
A Convenient Total Synthesis of (+/-)-Isoochracinic Acid, a Phthalide from Alternaria kikuchiana
Yeola, Suresh N.,Mali, R. S.
, p. 804 - 806 (2007/10/02)
Total synthesis of (+/-)-isoochracinic acid (7), starting from 2-formyl-6-methoxybenzoic acid (3) as the key intermediate is described.Compound (3) is obtained by heteroatom directed lithiation reaction on 2-methoxy-N-methylbenzamide (1).
Regiocontrolled Synthesis of Hydroxyphthalides. Synthesis of (+/-)-Isoochracinic Acid and a Zealeranone Intermediate
Trost, Barry M.,Rivers, Gordon T.,Gold, Jeffrey M.
, p. 1835 - 1838 (2007/10/02)
Metalation of 3-methoxy- and 3,5-dimethoxybenzyl alcohol followed by quenching with CO2 provided the phthalides.Bromination and solvolysis generated 7-methoxy- and 5,7-dimethoxyphthalaldehydic acid in a fully regiocontrolled reaction.The former served as
