Total synthesis of (+)-batzelladine A and (-)-batzelladine D via [4+2]-annulation of vinyl carbodiimides with N-alkyl imines Journal Article
| Authors: | Arnold, M. A.; Day, K. A.; Durón, S. G.; Gin, D. Y. |
| Article Title: | Total synthesis of (+)-batzelladine A and (-)-batzelladine D via [4+2]-annulation of vinyl carbodiimides with N-alkyl imines |
| Abstract: | A diastereoselective [4 + 2]-annulation of vinyl carbodiimides with chiral N-alkyl imines has been developed to access the stereochemically rich polycyclic guanidine cores of the batzelladine alkaloids. Application of this strategy, together with additional key steps such as long-range directed hydrogenation and diastereoselective intramolecular iodo-amination, led to highly convergent total syntheses of (-)-batzelladine D and (+)- batzelladine A with excellent stereocontrol. |
| Keywords: | alkaloids; stereochemistry; cycloaddition; group; hydrogenation; enantioselective total-synthesis; absolute-configuration; tricyclic guanidinium core; batzelladine-a; structural revision; hydroxyl |
| Journal Title: | Journal of the American Chemical Society |
| Volume: | 128 |
| Issue: | 40 |
| ISSN: | 0002-7863 |
| Publisher: | American Chemical Society |
| Date Published: | 2006-10-11 |
| Start Page: | 13255 |
| End Page: | 13260 |
| Language: | English |
| ACCESSION: | WOS:000241030500043 |
| DOI: | 10.1021/ja063860+ |
| PROVIDER: | wos |
| PMCID: | PMC2610335 |
| PUBMED: | 17017806 |
| Notes: | --- - Article - "Source: Wos" |
