吡咯烷
电化学
全合成
戒指(化学)
分子
组合化学
化学
立体化学
有机化学
电极
物理化学
作者
B. V. Smith,Nathanyal J. Truax,Alexandros Pollatos,Michael Meanwell,Pranali Bedekar,Alberto F. Garrido‐Castro,Phil S. Baran
标识
DOI:10.1002/anie.202401107
摘要
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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