Mycophenolic acid (28) has been obtained by a convergent synthesis starting from methyl 6-bromo-4-methylhex-4-enoate (13) and 5,7-dihydroxy-4-methylphthalide (24). For the total synthesis of 5,7-dihydroxy-4-methylphthalide, 1-carbethoxy-2,3-dimethylcyclohexa-4,6-dione (14) was aromatized and transformed into 4,6-dimethoxy-2,3-dimethylbenzamide. The photolysis of the corresponding N-chloroamide and subsequent hydrolysis gave 5,7-dimethoxy-4-methylphthalide which was hydrolysed to 5,7-dihydroxy-4-methylphthalide (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. © 1972.
A total synthesis of mycophenolic acid, some analogues and some biogenetic intermediates / L. Canonica, B. Rindone, E. Santaniello, C. Scolastico. - In: TETRAHEDRON. - ISSN 0040-4020. - 28:16(1972), pp. 4395-4404.
Titolo: | A total synthesis of mycophenolic acid, some analogues and some biogenetic intermediates |
Autori: | SANTANIELLO, ENZO (Penultimo) SCOLASTICO, CARLO (Ultimo) |
Settore Scientifico Disciplinare: | Settore BIO/10 - Biochimica |
Data di pubblicazione: | 1972 |
Rivista: | |
Tipologia: | Article (author) |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1016/S0040-4020(01)88962-6 |
Appare nelle tipologie: | 01 - Articolo su periodico |