AI Article Synopsis
- The text discusses the first successful total synthesis of dragocins A-C, which are unique natural products with a distinctive C4' oxidized ribose structure connected by a polyhydroxylated pyrrolidine.
- The synthesis process involved several complex steps, including a notable failure when trying to perform a C-H oxidation on an important intermediate.
- The final synthesis method included an efficient approach for creating a complex pyrrolidine and a novel selective electrochemical oxidation that produced a characteristic 9-membered ring, suggesting this technique could be broadly applicable in future research.
Article Abstract
The first total synthesis of dragocins A-C, remarkable natural products containing an unusual C4' oxidized ribose architecture bridged by a polyhydroxylated pyrrolidine, is presented through a route featuring a number of uncommon maneuvers. Several generations towards the target molecules are presented, including the spectacular failure of a key C-H oxidation on a late-stage intermediate. The final route features rapid, stereocontrolled access to a densely functionalized pyrrolidine and an unprecedented diastereoselective oxidative electrochemical cyclization to forge the hallmark 9-membered ring. Preliminary studies suggest this electrochemical oxidation protocol is generally useful.
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Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11619770 | PMC |
| http://dx.doi.org/10.1002/anie.202401107 | DOI Listing |
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