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|
SANTANIELLO, ENZO (Penultimo)
SCOLASTICO, CARLO (Ultimo)
|Settore Scientifico Disciplinare:||Settore BIO/10 - Biochimica|
|Data di pubblicazione:||1972|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1016/S0040-4020(01)88962-6|
|Appare nelle tipologie:||01 - Articolo su periodico|