The synthesis of the Securinega alkaloid secu'amamine E (ent-virosine A) has been accomplished for the first time in 12 steps and 8.5% overall yield. In addition, bubbialine has been prepared and characterized. These two alkaloids and bubbialidine, all featuring an azabicyclo[2.2.2]octane core, were rearranged to their azabicyclo[3.2.1]octane congeners, a framework found in many Securinega alkaloids. These experiments suggest that azabicyclo[2.2.2]octane derivatives could serve as intermediates in the biosynthesis of the rearranged azabicyclo[3.2.1]octane products.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.6b03716 | DOI Listing |
Publication Analysis
Top Keywords
securinega alkaloids
8
rearranged azabicyclo[321]octane
8
investigating biogenetic
4
biogenetic hypotheses
4
hypotheses securinega
4
alkaloids enantioselective
4
enantioselective total
4
total syntheses
4
syntheses secu'amamine
4
secu'amamine e/ent-virosine
4
Similar Publications
Want AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!