@article {47097,
	title = {Divergent approach to the synthesis of (-)-balanol heterocycle and cis-3-hydroxypipecolic acid based on chiral 2-aminoalkanol equivalent},
	journal = {Tetrahedron},
	volume = {80},
	year = {2021},
	month = {JAN},
	pages = {131773},
	type = {Article},
	abstract = {<p>Enantioselective synthesis of the hexahydroazepine core of (-)-balanol and formal synthesis of cis-3hydroxypipecolic acid from a common intermediate have been accomplished by a divergent path. The common intermediate was accessed from a favorably protected enantiomerically pure 2-amino-1,3,4-butanetriol (ABT) equivalent via oxidation and Wittig olefination. The synthesis of (-)-balanol heterocycle featured tandem reduction/acetal-deprotection/gamma-lactonization reaction and a one-pot azide reduction followed by seven membered aza-heterocycle formation while the route to cis-3-hydroxypipecolic acid highlighted the base induced piperidine ring formation and regioselective benzylidine-acetal cleavage. (C) 2020 Elsevier Ltd. All rights reserved.</p>
},
	keywords = {Amino-alcohol, desymmetrization, Hexahydroazepine, Piperidine alkaloids, Protein kinase},
	issn = {0040-4020},
	doi = {10.1016/j.tet.2020.131773},
	author = {Chavan, Subhash P. and Kalbhor, Dinesh B. and Gonnade, Rajesh G.}
}
