| Title : Stereodivergent synthesis of the LFA-1 antagonist BIRT-377 by porcine liver esterase desymmetrization and Curtius rearrangement - Johnson_2015_Org.Biomol.Chem_13_1463 |
| Author(s) : Johnson A , Saunders MJ , Back TG |
| Ref : Org Biomol Chem , 13 :1463 , 2015 |
|
Abstract :
The LFA-1 inhibitor and leukocyte adhesion suppressor BIRT-377 was prepared in high enantiomeric excess by desymmetrization of dimethyl 2-p-bromobenzyl-2-methylmalonate, followed by condensation of the resulting carboxylic acid with 3,5-dichloroaniline, saponification of the remaining ester and Curtius rearrangement as the key steps. When Curtius rearrangement preceded the condensation step, (ent)-BIRT-377 was similarly obtained in high ee. |
| PubMedSearch : Johnson_2015_Org.Biomol.Chem_13_1463 |
| PubMedID: 25474271 |
Johnson A, Saunders MJ, Back TG (2015)
Stereodivergent synthesis of the LFA-1 antagonist BIRT-377 by porcine liver esterase desymmetrization and Curtius rearrangement
Org Biomol Chem
13 :1463
Johnson A, Saunders MJ, Back TG (2015)
Org Biomol Chem
13 :1463