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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. Show more
Publication status
publishedExternal links
Journal / series
Angewandte Chemie. International EditionPages / Article No.
Publisher
WeinheimSubject
total synthesis; alkaloids; electrochemistryFunding
101027337 - Transition Metal Catalysis Towards Saturation in Organic Molecules through Alkyl Radical Chemistry (EC)
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ETH Bibliography
yes
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