Divergent approach to the synthesis of (-)-balanol heterocycle and cis-3-hydroxypipecolic acid based on chiral 2-aminoalkanol equivalent
| Title | Divergent approach to the synthesis of (-)-balanol heterocycle and cis-3-hydroxypipecolic acid based on chiral 2-aminoalkanol equivalent |
| Publication Type | Journal Article |
| Year of Publication | 2021 |
| Authors | Chavan, SP, Kalbhor, DB, Gonnade, RG |
| Journal | Tetrahedron |
| Volume | 80 |
| Pagination | 131773 |
| Date Published | JAN |
| Type of Article | Article |
| ISSN | 0040-4020 |
| Keywords | Amino-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. |
| DOI | 10.1016/j.tet.2020.131773 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.457 |