THE CHEMISTRY OF PSEUDOMONIC ACID. PART 9. REDUCTION, INVERSION AND REPLACEMENT OF THE C-13 HYDROXYL GROUP

Article abstract of DOI:10.1016/S0040-4020(01)86798-3

The preparations of methyl 13-deoxypseudomonate (2c) and methyl (13R)-monate (4f) via mesylate derivatives are described.Introduction of an amino function by nucleophilic displacement at the C-13 position was unsuccessful but the 13-amine (2f) was prepared via the o-methyloxime (7b) and lithium borohydride reduction.