AI Article Synopsis
- - We created a new strategy to synthesize a specific type of pyrrolidine using the unique reactions of sulfone and a cyclization process called 5-endo-trig.
- - Our method successfully produced the indolizidine alkaloid monomorine I, highlighting the importance of selecting the right nitrogen protecting group and optimal conditions for a key stereoselective amination step.
- - By combining various protecting groups and using an intramolecular reductive amination reaction, we synthesized (+)-monomorine I in only 11 steps from D-norleucine, achieving complete stereoselectivity.
Article Abstract
We have developed a general strategy for the synthesis of 2,5-syn disubstituted pyrrolidines that is based on the multi-faceted reactivity of the sulfone moiety and a 5-endo-trig cyclisation. This methodology was applied to the synthesis of indolizidine alkaloid monomorine I. Two factors were key to the success of this endeavour; the first was the choice of nitrogen protecting group whilst the second was the conditions for the final stereoselective amination step. Employing a combination of different protecting groups and an intramolecular reductive amination reaction we were able to prepare (+)-monomorine I in just 11 steps from commercially available D-norleucine in a completely stereoselective manner.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2151076 | PMC |
| http://dx.doi.org/10.1186/1860-5397-3-39 | DOI Listing |
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