Syntheses of Mycophenolic Acid and Its Analogs by Palladium Methodology

Autor:	Isao Shimizu, Katsuji Ujita, Miki Nagatomo, Hiroshi Ohta, Yasunari Fujiwara, Youngmin Lee
Rok vydání:	2001
Předmět:	chemistry.chemical_classification Iodide chemistry.chemical_element Alcohol General Chemistry Dimethyl malonate Toluene Catalysis Phthalide chemistry.chemical_compound chemistry Organic chemistry Carbonylation Palladium
Zdroj:	Bulletin of the Chemical Society of Japan. 74:1437-1443
ISSN:	1348-0634 0009-2673
DOI:	10.1246/bcsj.74.1437
Popis:	Syntheses of mycophenolic acid (MPA, 1) and its analogs were carried out using palladium-catalyzed Heck carbonylation and olefination. Thus, the reaction of 2-bromo-3,5-dimethoxybenzyl alcohol (4) in toluene under carbon monoxide at 180 °C in the presence of palladium catalyst using sodium carbonate as a base gave 5,7-dimethoxyphthalide (5) in 88% yield. The phthalide 7 was converted to 6-iodo-5,7-dimethoxy-4-methylphthalide (8). Reaction of aromatic iodide 8 with isoprene and dimethyl malonate in the presence of palladium(0) catalyst gave the three component coupling product 9, which was converted into 1 in three steps. 4-NorMPA (16) and 4-homoMPA (22) were synthesized similarly.
Databáze:	OpenAIRE
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