Enantioselective total syntheses of (-)-isonitramine, (-)-sibirine, and (+)-nitramine by ring-closing metathesis
| Title | Enantioselective total syntheses of (-)-isonitramine, (-)-sibirine, and (+)-nitramine by ring-closing metathesis |
| Publication Type | Journal Article |
| Year of Publication | 2011 |
| Authors | Pandey, G, Kumara, PC, Burugu, SKumar, Puranik, VG |
| Journal | European Journal of Organic Chemistry |
| Issue | 36 |
| Pagination | 7372-7377 |
| Date Published | DEC |
| ISSN | 1434-193X |
| Keywords | Alk-aloids, Allylation, Amino alcohols, Metathesis, Total synthesis |
| Abstract | Concise enantioselective total syntheses of naturally occurring 2-azaspiro[5,5]undecan-7-ol (Nitraria) alkaloids viz. ()-isonitramine, ()-sibirine, and (+)-nitramine are accomplished in 42, 38, and 25?% overall yield, respectively, in six steps starting from enantiomerically pure (S)-methyl 3-allyl-2-oxo-1,2,3,6-tetrahydropyridine-3-carboxylate (>99?%?ee). The key feature of the syntheses involves diastereoselective HosomiSakurai allylation followed by ring-closing metathesis. |
| DOI | 10.1002/ejoc.201101256 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 3.07 |
Divison category:
Center for Material Characterization (CMC)
Organic Chemistry