A total synthesis of mycophenolic acid, some analogues and some biogenetic intermediates

✍ Scribed by L. Canonica; B. Rindone; E. Santaniello; C. Scolastico

• Publisher: Elsevier Science
• Year: 1972
• Tongue: French
• Weight: 725 KB
• Volume: 28
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)88962-6

✦ Synopsis

Abatrac-Mycophenolic acid (28) has been obtained by a convergent synthesis starting from methyl 6bromo4methyIhex4enoate (13) and 5,7dihydroxy4methylphthalide (24). For the total synthesis of 5,7dihydroxy4methylphthalide, l-carbethoxy-2,3-dimethylcyclohexa+-dione (14) was aromatized and transformed into 4,6-dimelhoxy-2,3dimethylbenzamide. The photolysis of the corresponding Nchloroamide and subsequent hydrolysis gave 5,7-dimethoxy4methylphthalide which was hydrolysed to 5,7-dihydroxy4methylphthalide (24). The bromoester (13) was obtained starting from geraniol. Condensation between 13 and 24 with silver oxide in dioxane afforded the methyl ester of nor-O-methyl mycophenolic acid. Selective methylation and hydrolysis furnished mycophenolic acid.