TY - JOUR
T1 - Syntheses of mycophenolic acid and its analogs by palladium methodology
AU - Lee, Y.
AU - Fujiwara, Y.
AU - Ujita, K.
AU - Nagatomo, M.
AU - Ohta, H.
AU - Shimizu, I.
PY - 2001/8
Y1 - 2001/8
N2 - 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.
AB - 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.
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U2 - 10.1246/bcsj.74.1437
DO - 10.1246/bcsj.74.1437
M3 - Article
AN - SCOPUS:0034843344
SN - 0009-2673
VL - 74
SP - 1437
EP - 1443
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
IS - 8
ER -