1.
J Vasc Surg Venous Lymphat Disord
; 2(1): 115-6, 2014 Jan.
Article
in English
| MEDLINE
| ID: mdl-26993012
2.
Bioorg Med Chem Lett
; 9(13): 1881-4, 1999 Jul 05.
Article
in English
| MEDLINE
| ID: mdl-10406659
ABSTRACT
A simple synthesis of phenylphosphonate monoester analogues of the transition state for hydrolysis of the benzoyl ester group in cocaine is provided by the reaction of 2beta-amido-3beta-tropanols with phenylphosphonyl dichloride. Steric hindrance to phosphonylation of the hydroxyl is overcome because the neighbouring 2beta-amido group participates in the reaction. The intramolecular assistance by the amide to formation of the phosphonate ester is influenced by the electronic environment of the amide group.