@article {46435,
	title = {Enantioselective formal total synthesis of (-)-quinagolide},
	journal = {Organic Letters},
	volume = {21},
	year = {2019},
	month = {NOV},
	pages = {9089-9093},
	type = {Article},
	abstract = {<p>The enantioselective formal total synthesis of (-)-quinagolide has been accomplished in a linear sequence of 8 purification steps from pyridine. The key steps are (a) organocatalyzed Diets-Alder reaction for fixing all three stereocenters on piperidine ring; (b) protecting group enabled deoxygenation of isoquinuclidine skeleton under Birch reduction condition; (c) Lewis acid (TiCl4) catalyzed intramolecular Friedel-Crafts cyclization of dicarboxylic acid; and (d) one-pot diastereoselective ketone reduction-intramolecular cyclization to form oxazolidinone which enables trans-geometry installation. During the course of the synthesis, an interesting reductive cleavage of the C-N bond in the electron-deficient isoquinuclidine skeleton under the Birch reduction conditions has been observed. This is the first synthetic effort to access the core skeleton of (-)-quinagolide.</p>
},
	issn = {1523-7060},
	doi = {10.1021/acs.orglett.9b03477},
	author = {Chavan, Subhash P. and Kadam, Appasaheb L. and Gonnade, Rajesh G.}
}
