Asymmetric synthetic access to the hetisine alkaloids: Total synthesis of (+)-nominine Journal Article
| Authors: | Peese, K. M.; Gin, D. Y. |
| Article Title: | Asymmetric synthetic access to the hetisine alkaloids: Total synthesis of (+)-nominine |
| Abstract: | A dual cycloaddition strategy for the synthesis of the hetisine alkaloids has been developed, illustrated by a concise asymmetric total synthesis of (+)-nominine (7). The approach relies on an early-stage intramolecular 1,3-dipolar cyclo-addition of a 4-oxido-isoquinolinium betaine dipole with an ene-nitrile dipolarophile. Subsequent late-stage pyrrolidine-induced dienamine isomerization/Diels-Alder cascade allows for rapid construction of the carbon-nitrogen polycyclic skeleton within this class of C20- diterpenoid alkaloids. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA. |
| Keywords: | alkaloids; cycloaddition; natural products; asymmetric synthesis; hetisine; cyanides |
| Journal Title: | Chemistry - A European Journal |
| Volume: | 14 |
| Issue: | 5 |
| ISSN: | 0947-6539 |
| Publisher: | Wiley V C H Verlag Gmbh |
| Date Published: | 2008-02-08 |
| Start Page: | 1654 |
| End Page: | 1665 |
| Language: | English |
| DOI: | 10.1002/chem.200701290 |
| PROVIDER: | scopus |
| PMCID: | PMC2648811 |
| PUBMED: | 18046691 |
| DOI/URL: | |
| Notes: | --- - "Cited By (since 1996): 7" - "Export Date: 17 November 2011" - "CODEN: CEUJE" - "Source: Scopus" |
