Total synthesis of (+/-)/(+)-subincanadine E and determination of absolute configuration
| Title | Total synthesis of (+/-)/(+)-subincanadine E and determination of absolute configuration |
| Publication Type | Journal Article |
| Year of Publication | 2017 |
| Authors | Kalshetti, MG, Argade, NP |
| Journal | Journal of Organic Chemistry |
| Volume | 82 |
| Issue | 20 |
| Pagination | 11126-11133 |
| Date Published | OCT |
| Type of Article | Article |
| Abstract | A facile synthesis of (+/-)-subincanadine E was described from tryptamine-based maleimide. 1,2-Addition of Grignard reagent to maleimide, internal activation of formed lactamol for in situ 1,4-addition of Grignard reagent, and associated position-specific allylic rearrangement in diastereoselective Pictet-Spengler cyclization were the key steps. Enantioselective first total synthesis of naturally occurring cytotoxic (+)-subincanadine E was also accomplished from (S)-acetoxysuccinimide via an unusual syn-addition of cuprate to the alpha/beta-unsaturated lactam. Sinister absolute configuration was assigned to (+)-subincanadine E on the basis of total synthesis. (S)-Acetoxy group in the succinimide precursor was initially employed to impart regio- and stereoselectivity and then as a suitable leaving group to generate the desired conjugated lactam. |
| DOI | 10.1021/acs.job.7b02122 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 4.849 |
Divison category:
Organic Chemistry