Synthesis of 2-azabicyclo[m.n.0]-alkanes and their application towards the synthesis of strychnos and stemona classes of alkaloids
| Title | Synthesis of 2-azabicyclo[m.n.0]-alkanes and their application towards the synthesis of strychnos and stemona classes of alkaloids |
| Publication Type | Journal Article |
| Year of Publication | 2020 |
| Authors | Majumder, B, Pandey, G |
| Journal | European Journal of Organic Chemistry |
| Volume | 2020 |
| Issue | 25 |
| Pagination | 3883-3888 |
| Date Published | JUL |
| Type of Article | Article |
| ISSN | 1434-193X |
| Keywords | alkaloids, amines, Grignard reaction, Michael addition, Natural products |
| Abstract | 2-Azabicyclo[m.n.0]alkane ring systems, the conceptual precursors towards the synthesis of Strychnos and Stemona classes of alkaloids, were synthesized from tert-butyl 2-(phenylsulfonyl)-7-aza-bicyclo[2.2.1]hept-2-ene-7-carboxylate by alkyl Grignard reaction and intramolecular cyclisation of the in situ generated ring opening product 2. The synthesized cis-hexahydroindole 3 and cis-octahydro-benzo[b]azepine 5 scaffolds were utilized to construct the advanced intermediates 25 and 35, respectively, towards the synthesis of the corresponding Strychnos and Stemona classes of alkaloids. |
| DOI | 10.1002/ejoc.202000507, Early Access Date = MAY 2020 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.889 |
Divison category:
Organic Chemistry