Divergent approach to the synthesis of (-)-balanol heterocycle and cis-3-hydroxypipecolic acid based on chiral 2-aminoalkanol equivalent

TitleDivergent approach to the synthesis of (-)-balanol heterocycle and cis-3-hydroxypipecolic acid based on chiral 2-aminoalkanol equivalent
Publication TypeJournal Article
Year of Publication2021
AuthorsChavan, SP, Kalbhor, DB, Gonnade, RG
JournalTetrahedron
Volume80
Pagination131773
Date PublishedJAN
Type of ArticleArticle
ISSN0040-4020
KeywordsAmino-alcohol, desymmetrization, Hexahydroazepine, Piperidine alkaloids, Protein kinase
Abstract

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.

DOI10.1016/j.tet.2020.131773
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)2.457
Divison category: 
Center for Material Characterization (CMC)
Organic Chemistry

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