Rapid bioinspired N-acyliminium ion strategy for the ABC core of the stemona alkaloids
| Title | Rapid bioinspired N-acyliminium ion strategy for the ABC core of the stemona alkaloids |
| Publication Type | Journal Article |
| Year of Publication | 2023 |
| Authors | Chavan, SP, Kalbhor, DB, Gonnade, RG |
| Journal | Asian Journal of Organic Chemistry |
| Volume | 12 |
| Issue | 9 |
| Date Published | SEP |
| Type of Article | Article |
| ISSN | 2193-5807 |
| Keywords | alkaloids, Biomimetic synthesis, Claisen rearrangement, cyclization, Regioselectivity |
| Abstract | A concise and highly diastereoselective bioinspired key cationic cyclization strategy for the asymmetric synthesis of the tricyclic core of the (-)-stemoamide, together with 8,9-bis-epi-stemoamide has been described. The key N-acyliminium ion precursors were accessed from L-tartaric acid and L-malic acid respectively. The use of ethyl acetoacetate derived bifunctional allylidenetriphenylphosphorane reagent in the early stage of the synthetic strategy is advantageous for the rapid construction of highly functionalized key pyrrolo[1,2-& alpha;]azepine frameworks. |
| DOI | 10.1002/ajoc.202300331 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.7 |
Divison category:
Center for Material Characterization (CMC)
Organic Chemistry
Database:
Web of Science (WoS)
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