Syntheses of mycophenolic acid and its analogs by palladium methodology

Y. Lee, Y. Fujiwara, K. Ujita, M. Nagatomo, H. Ohta, I. Shimizu

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Abstract

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.

Original languageEnglish
Pages (from-to)1437-1443
Number of pages7
JournalBulletin of the Chemical Society of Japan
Volume74
Issue number8
DOIs
Publication statusPublished - 2001 Aug

ASJC Scopus subject areas

  • Chemistry(all)

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    Lee, Y., Fujiwara, Y., Ujita, K., Nagatomo, M., Ohta, H., & Shimizu, I. (2001). Syntheses of mycophenolic acid and its analogs by palladium methodology. Bulletin of the Chemical Society of Japan, 74(8), 1437-1443. https://doi.org/10.1246/bcsj.74.1437