Journal
TETRAHEDRON
Volume 80, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2020.131773
Keywords
Hexahydroazepine; Amino-alcohol; Protein kinase; Desymmetrization; Piperidine alkaloids
Categories
Funding
- UGC, New Delhi, India
- CSIR, New Delhi, India [CSC-0108, CSC-0301]
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Enantioselective synthesis of the hexahydroazepine core of (-)-balanol and formal synthesis of cis-3-hydroxypipecolic acid were 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.
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.
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