Syntheses of mycophenolic acid and its analogs by palladium methodology

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

研究成果: Article

31 引用 (Scopus)

抄録

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.

元の言語English
ページ(範囲)1437-1443
ページ数7
ジャーナルBulletin of the Chemical Society of Japan
74
発行部数8
DOI
出版物ステータスPublished - 2001 8

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Mycophenolic Acid
Palladium
Carbonylation
Catalysts
Toluene
Iodides
Carbon Monoxide
Alcohols

ASJC Scopus subject areas

  • Chemistry(all)

これを引用

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

Syntheses of mycophenolic acid and its analogs by palladium methodology. / Lee, Y.; Fujiwara, Y.; Ujita, K.; Nagatomo, M.; Ohta, H.; Shimizu, I.

:: Bulletin of the Chemical Society of Japan, 巻 74, 番号 8, 08.2001, p. 1437-1443.

研究成果: Article

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