Regioselective and stereoselective reductive aziridinium ring cleavage leading to azabicyclodecane architecture: enantioselective synthesis of (+)-subincanadine F
| Title | Regioselective and stereoselective reductive aziridinium ring cleavage leading to azabicyclodecane architecture: enantioselective synthesis of (+)-subincanadine F |
| Publication Type | Journal Article |
| Year of Publication | 2018 |
| Authors | Kalshetti, MG, Argade, NP |
| Journal | Journal of Organic Chemistry |
| Volume | 83 |
| Issue | 19 |
| Pagination | 12164-12170 |
| Date Published | OCT |
| Type of Article | Article |
| ISSN | 0022-3263 |
| Abstract | Enantioselective synthesis of cytotoxic indole alkaloid (+)-subincanadine F was accomplished starting from the corresponding (S)-acetoxysuccinimide via aziridinium ring formation and its reductive ring expansion route. Regioselective and stereoselective reductive aziridinium carbon-nitrogen bond cleavage comprising ring expansions was a key step. The (S)-OMOM protection of the hydroxyl moiety adjacent to a benzylic carbon of an in situ formed aziridinium system was necessary for lithium borohydride-induced reductive ring expansions, and it also served as a latent source of an essential ketone carbonyl group for the generation of an alpha,beta-conjugated system. |
| DOI | 10.1021/acs.joc.8b02113 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 4.805 |
Divison category:
Organic Chemistry