Furan-derived chiral bicycloaziridino lactone synthon: collective syntheses of oseltamivir phosphate (Tamiflu), (S)-pipecolic acid and its 3-hydroxy derivatives
| Title | Furan-derived chiral bicycloaziridino lactone synthon: collective syntheses of oseltamivir phosphate (Tamiflu), (S)-pipecolic acid and its 3-hydroxy derivatives |
| Publication Type | Journal Article |
| Year of Publication | 2020 |
| Authors | Chavan, SP, Kadam, AL, Shinde, SS, Gonnade, RG |
| Journal | Chemistry-An Asian Journal |
| Volume | 15 |
| Issue | 3 |
| Pagination | 415-424 |
| Date Published | FEB |
| Type of Article | Article |
| ISSN | 1861-4728 |
| Keywords | Aziridine synthon, Chiral auxiliary, collective synthesis, Pipecolic acid, Tamiflu |
| Abstract | A unified synthetic strategy for oseltamivir phosphate (tamiflu), (S)-pipecolic acid, and its 3-hydroxy derivatives from furan derived common chiral bicycloaziridino lactone synthon is described here. Key features are the short (4-steps), enantiopure, and decagram-scale synthesis of common chiral synthon from furan and its first-ever application in the total synthesis of biologically active compounds by taking the advantages of high functionalization ability of chiral synthon. |
| DOI | 10.1002/asia.201901523, Early Access Date = JAN 2020 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 4.056 |
Divison category:
Organic Chemistry
Physical and Materials Chemistry