01580nas a2200181   4500008004100000022001400041245019800055210006900253260000900322300001400331490000700345520082500352100002401177700002501201700002601226700002401252856012201276       2018                        eng d  a1523-706000aSynthesis of 3-azidopiperidine skeleton employing ceric ammonium nitrate (CAN)-mediated regioselective azidoalkoxylation of enol ether: total synthesis of d-2 receptor agonist (+/-)-quinagolide0 aSynthesis of 3azidopiperidine skeleton employing ceric ammonium   cNOV   a7011-70140 v203 aThe total synthesis of (+/-)-quinagolide, which is a D-2 receptor agonist, was accomplished via a ceric ammonium nitrate (CAN)-mediated regioselective azidoalkoxylation of enol ether route. Key features of the synthesis include Claisen rearrangement, PPTS (pyridinium p-toluene-sulfonate)-catalyzed one-pot acetal deprotection, followed by a diastereoselective Henry reaction, which enables construction of the required trans ring junction and CAN-mediated regioselective azidoalkoxylation of enol ether. The PPTS-catalyzed intramolecular diastereoselective Henry reaction to fix three contiguous stereocenters on tetrahydronaphthalene and the first-of-its-kind synthesis of the 3-azidopiperidine skeleton, using a CAN -mediated regioselective azidoalkoxylation of enol ether, are important findings of the present work.1 aChavan, Subhash, P.1 aKadam, Appasaheb, L.1 aLasonkar, Pradeep, B.1 aGonnade, Rajesh, G.  uhttps://library.ncl.res.in/content/synthesis-3-azidopiperidine-skeleton-employing-ceric-ammonium-nitrate-can-mediated