Returning to the pivotal electrochemical cyclization reaction, the premise that these conditions may be amenable towards the preparation of benzylic b-hydroxy amino acids was explored (Figure ). Typical conditions employed for such a transformation often suffer from poor reactivity 17 or require a stepwise protocol. Slight modification of the conditions presented above proved successful in generating a small series of oxazolidinones which may prove useful in the synthesis of functionalized b-hydroxy amino acid building blocks (17-20). A more indepth study of this method is therefore warranted to fully tease out its generality. A simple solution to the challenge posed by the dragocin natural product family has been presented. The successful route features a number of interesting transformations that may find application in other settings, such as: (1) rapid, stereocontrolled entry to polyhydroxylated pyrrolidines through diastereoselective and regioselective reactions, (2) rAP-mediated electrochemical metal-free tosylamide removal, (3) one-pot decarboxylative Barton chlorination, and, most remarkably, (4) oxidative, diastereoselective C-H functionalizing electrochemical cyclization to form a 9-membered ring. Authors are required to submit a graphic entry for the Table of Contents (TOC) that, in conjunction with the manuscript title, should give the reader a representative idea of one of the following: A key structure, reaction, equation, concept, or theorem, etc., that is discussed in the manuscript. Consult the journal's Instructions for Authors for TOC graphic specifications.