Enantioselective total syntheses of (-)-isonitramine, (-)-sibirine, and (+)-nitramine by ring-closing metathesis

TitleEnantioselective total syntheses of (-)-isonitramine, (-)-sibirine, and (+)-nitramine by ring-closing metathesis
Publication TypeJournal Article
Year of Publication2011
AuthorsPandey, G, Kumara, PC, Burugu, SKumar, Puranik, VG
JournalEuropean Journal of Organic Chemistry
Date PublishedDEC
KeywordsAlk-aloids, Allylation, Amino alcohols, Metathesis, Total synthesis

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.

Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)3.07
Divison category: 
Center for Material Characterization (CMC)
Organic Chemistry