@article {45487,
	title = {Synthesis of 3-azidopiperidine skeleton employing ceric ammonium nitrate (CAN)-mediated regioselective azidoalkoxylation of enol ether: total synthesis of d-2 receptor agonist (+/-)-quinagolide},
	journal = {Organic letters },
	volume = {20},
	year = {2018},
	month = {NOV },
	pages = {7011-7014},
	type = {Article },
	abstract = {The 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.},
	issn = {1523-7060},
	doi = { 10.1021/acs.orglett.8b02900},
	author = {Chavan, Subhash P. and Kadam, Appasaheb L. and Lasonkar, Pradeep B. and Gonnade, Rajesh G.}
}
