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- Title
Total Synthesis of Dragocins A−C through Electrochemical Cyclization.
- Authors
Smith, Brendyn P.; Truax, Nathanyal J.; Pollatos, Alexandros S.; Meanwell, Michael; Bedekar, Pranali; Garrido‐Castro, Alberto F.; Baran, Phil S.
- 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.
- Subjects
RING formation (Chemistry); NATURAL products; RIBOSE; PYRROLIDINE; OXIDATION; MOLECULES
- Publication
Angewandte Chemie, 2024, Vol 136, Issue 19, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202401107