01589nas a2200229   4500008004100000022001400041245014100055210006900196260000800265300001100273490000700284520076600291653001801057653002101075653002101096653002501117653001901142100002401161700002401185700002401209856012601233       2021                        eng d  a0040-402000aDivergent approach to the synthesis of (-)-balanol heterocycle and cis-3-hydroxypipecolic acid based on chiral 2-aminoalkanol equivalent0 aDivergent approach to the synthesis of balanol heterocycle and c  cJAN  a1317730 v803 a<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>
10aAmino-alcohol10adesymmetrization10aHexahydroazepine10aPiperidine alkaloids10aProtein kinase1 aChavan, Subhash, P.1 aKalbhor, Dinesh, B.1 aGonnade, Rajesh, G.  uhttps://library.ncl.res.in/content/divergent-approach-synthesis-balanol-heterocycle-and-cis-3-hydroxypipecolic-acid-based